New and convenient synthesis of acyl isocyanates was written by Speziale, A. J.;Smith, L. R.. And the article was included in Journal of Organic Chemistry in 1962.Electric Literature of C7H5Cl2NO This article mentions the following:
A new and convenient synthesis of acyl isocyanates (I) which involved the reaction of primary amides with oxalyl chloride (II) was described. A suspension of the amide in C2H4Cl2 was treated with excess II, the mixture refluxed 4-16 h., evaporated, and I isolated by distillation in vacuo. The following I (RCONCO) were thus obtained (R, % yield, b.p./mm. given): ClCH2, 64, 50-5°/20; Cl2CH, 68, 135°/35; Cl3C, 60, 80-5°/20; PhCH2, 36, 85°/3; 3,4-Cl2C6H3, 97, 105-5°/1.6; Ph, 75, 97-8°/23; Ph2CH, 37, 136-40°/1.0-1.2. I were readily hydrolyzed on treatment with H2O. Acyl ureas, carbamates, and thiocarbamates were formed on reaction with amines, alcs., and mercaptans. Diacyl ureas were isolated in small yield in some cases as side products.. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Electric Literature of C7H5Cl2NO).
3,4-Dichlorobenzamide (cas: 2670-38-4) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Electric Literature of C7H5Cl2NO
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics