Month: November 2020

1943-79-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1943-79-9 name is Phenyl methylcarbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 10 Synthesis of N-methyl-N’-phenyl urea: 15.1 g. of phenyl N-methylcarbamate, 9.3 g. of aniline and 5.4 g. of the tetraethylammonium salt of 2-hydroxy-5-nitro-pyridine are refluxed in 200 ml. of ethanol for 5 hours. The reaction solution is concentrated, and the residue is dissolved in 100 ml. of chloroform, washed successively with 50 ml. of 1N sodium carbonate, 50 ml. of 1N hydrochloric acid and 100 ml. of water, and dried. By concentrating to dryness and recrystallizing from 120 ml. of ethanol, crystals of N-methyl-N-phenylurea having a m.p. of 150 – 151C. are obtained in 91% yield. When phenyl N-methyldithiocarbamate is used in place of phenyl N-methylcarbamate, N-methyl-N’-phenylthiourea is obtained in 79% yield, m.p. 113C. In either case, the reaction rate is considerably lower without the catalyst than with the catalyst.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Kyowa Hakko Kogyo Co., Ltd.; US3963728; (1976); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 108468-00-4.

General procedure: A solution of 4-(Boc-aminomethyl)benzylamine (3) (1.0 mmol) and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with an ice bath, then the corresponding sulfochloride (1.1 mmol, dissolved in 2 mL anhydrous DCM) was added dropwise. The reaction mixture was allowed to stir at 0 C for 1 h. After removing the cooling bath, the resulting mixture was stirred for 5 h at room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10 mL) for three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (150:1, v/v) to give the product as a white solid.

The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Gurbani, Saumya; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 360 – 371;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0, The chemical industry reduces the impact on the environment during synthesis 7341-96-0, name is Propiolamide, I believe this compound will play a more active role in future production and life.

The imine (0.2mmol), rhodium acetate (0.002mmol), Molecular sieve (300 mg) and the mixture is dissolved 1.5 ml dichloromethane solvent, into mixed solution 1, in 20 C stirring for 10 minutes. Then the propargyl amide (0.24mmol) and phenyl diazonium acetic acid methyl ester (0.24mmol) dissolved in 1.0 ml methylene chloride solvent, into solution 2. The solution 2 for 20 C lower, in 1 hour for adding and mixing the solution in the injection pump 1. The reaction mixture is purified by rapid column chromatography, to obtain the pure product, its structure is formula (b) is shown. The yield is 87%, dr value is equal to the 89:11.

The chemical industry reduces the impact on the environment during synthesis Propiolamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EAST CHINA NORMAL UNIVERSITY; HU, WENHAO; WU, YONG; WANG, WENKE; TANG, MIN; (29 pag.)CN106146334; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 27366-72-9, name is 2-(Dimethylamino)ethanethioamide hydrochloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 27366-72-9

EXAMPLE 9 Preparation of N-methyl-N’-2-([2-(dimethylaminomethyl)-5-methyl-4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine Following the procedure of Example 1, a reaction mixture containing 33.88 g. of ethyl 2-oxo-3-bromobutyrate [prepared by the procedure of Siefert et al., Helv. Chim. Acta, 33 725 (1950)], 21.52 g. of dimethylaminothioacetamide hydrochloride and 100 ml. of anhydrous ethanol was stirred and heated to refluxing temperature for about 2.5 hours. The reaction mixture was allowed to remain at room temperature overnight after which time it was concentrated by evaporation in vacuo. 100 ml. of an ice-water mixture was added to the resulting residue and the aqueous layer extracted with ethyl acetate. The ethyl acetate layer was discarded. The aqueous layer was cooled and then made basic (pH=11) with 2 N aqueous sodium hydroxide. The resulting alkaline layer was extracted several times with an equal volume of ethyl acetate and the ethyl acetate extracts were combined. The combined extracts were washed with water, with saturated aqueous sodium chloride, and were then dried. Concentration in vacuo provided a reddish oil comprising ethyl 2-(dimethylaminomethyl)-5-methyl-4-thiazolecarboxylate. Yield=21.2 g. (57%)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 27366-72-9.

Reference:
Patent; Eli Lilly and Company; US4375547; (1983); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

749927-69-3, The chemical industry reduces the impact on the environment during synthesis 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

The bromobenzamide A-2 (10 g, 43.1 mmol), aminoisobutyric acid B-l (6.7 g, 64.6 mmol, 1.5 equiv), K2C03 (15 g, 2.5 equiv), 99% CuCl (0.8 g, 8.1 mmol, 0.2 equiv), DMF (60 mL, 6 vol) and water (1.8 mL) were added to the flask and the reaction slurry was heated to 30 C. 2-Acetylcyclohexanone (1.14 mL, 8.1 mmol, 0.2 equiv) was added to the reaction slurry followed by stirring at 105 C under nitrogen for 12-14 h. HPLC analysis showed 96.6% conversion to the desired product. The reaction mixture was then cooled to RT and extracted with water (120 mL) and IP Ac (60 mL). The lower aqueous layer was re-extracted with IP Ac (60 mL) and acidified with 180 mL of 1M citric acid to a pH of 4.0. The product began to crystallize at RT and the batch was further cooled to 5-7 C, filtered, washed with water (40 mL) and dried under vacuum at 50 C for 12 h. The reaction yielded 8.3 g of product C-1 (75.4% yield) as a tan solid with HPLC purity of 99.6%.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-fluoro-N-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott; WO2011/106570; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

563-83-7, The chemical industry reduces the impact on the environment during synthesis 563-83-7, name is Isobutyramide, I believe this compound will play a more active role in future production and life.

A solution of 2-methylpropanamiotade (6 53 g, 75 0 mmol) and 2,4-biotas(4- methoxyphenyl)-1 ,3-diotathiotaa-2,4-diotaphosphetane-2,4-diotasulfiotade (15 17 g, 37 51 mmol) in THF (100 mL) was heated to reflux for 4 h The reaction mixture was then cooled to rt and poured into saturated aqueous NaHCO3 (200 mL) The mixture was extracted with ether (4 x 100 mL) The organic fractions were combined, dried over Na2SO4, filtered, and concentrated Purification by flash column chromatography (20% EtOAc hexanes) afforded 4 77 g (62%) of the title compound of Step A 1H-NMR (400 MHz, CDCI3) delta 7 63 (brs, 1 H), 6 90 (brs, 1 H), 2 88 (m, 1 H), and 1 27 (d, 6H, J = 6 8 Hz)

The chemical industry reduces the impact on the environment during synthesis Isobutyramide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 239074-29-4

To a mixture of 7-fluoro-8-hydroxy-l-methyl-2(lH)-quinoxalinone (150 mg), 1,1- dimethylethyl [tralpha/?5-4-(hydroxymethyl)cyclohexyl] carbamate (142 mg, 0.618 mmol, for a preparation see Example l(g)) and triphenylphosphine (195 mg, 0.742 mmol) in THF (10 mL) was added DIAD (0.144 mL, 0.742 mmol) and the mixture was stirred at rt for 1 h then triphenylphosphine (195 mg, 0.742 mmol) and DIAD (0.144 mL, 0.742 mmol) were added and the reaction was stirred at rt overnight. The solvent was evaporated and the residue was purified using silica chromatography (0-20%CH3CN/DCM) to afford the title compound (272 mg) which was used in the next step without further purification. MS (ES+) m/z 423 [MNH4+].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 239074-29-4.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1565-17-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1565-17-9, name is 4-Acetylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An amountof acetic acid glacial was added to a mixture of acetophenoneand phenyl hydrazine derivatives in 20 ml ethanol (EtOH),and the reaction was reBuxed overnight at 70C. Ethanol wasremoved under reduced pressure and the produced solidproduct was used without further puri7cation for pyrazolesynthesis.

The synthetic route of 4-Acetylbenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Assali, Mohyeddin; Abualhasan, Murad; Sawaftah, Hadeel; Hawash, Mohammed; Mousa, Ahmed; Journal of Chemistry; vol. 2020; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 239074-29-4 as follows.

To a solution of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate (0.84 g, 3.65 mmol) in THF (15 mL) was added No.23 triphenylphosphine (1.43 g, 5.45 mmol) and No.23 4,6-dichloropyrimidin-5-ol (0.68 g, 3.65 mmol). To the mixture was added No.23 diisopropylazodicarboxylate (1.47 g, 7.27 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=40:1 as eluent) to afford the tert-butyl (trans-4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexyl)carbamate as colorless oil (0.45 g, 33% yield). LC/MS APCI: Calculated 375.11; Observed m/z [M-99 (boc)]+ 276.1. 1H-NMR 400 MHz, DMSO-d6: delta 8.68 (s, 1H), 6.75 (d, J=7.60 Hz, 1H), 3.94 (d, J=6.00 Hz, 2H), 3.16-3.14 (m, 1H), 1.89-1.79 (m, 4H), 1.73-1.71 (m, 1H), 1.38 (s, 9H), 1.19-1.16 (m, 4H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

631-58-3,Some common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 9 A mixture of 3.6 parts of propanethioamide, 8.6 parts of 2-bromo-1-(4-hydroxyphenyl)ethanone and 79 parts of ethanol was stirred for 7 hours at reflux temperature. The reaction mixture was concentrated to 1/4 of its volume and 2,2′-oxybispropane was added to the residue. The precipitate was filtered off and taken up in water. After basifying with NH4 OH, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 3.3 parts (40.2%) of 4-(2-ethyl-4-thiazolyl)-phenol (interm. 17).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Propanethioamide, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica N.V.; US5100893; (1992); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics