Synthesis of diphenylcarbamoyl chloride

Preparation of diphenylcarbamoyl chloride

Alternative Names: N,N-diphenylcarbamoyl chloride; carbamic chloride, diphenyl-; diphenylcarbamic chloride

Preparation of diphenylcarbamoyl chloride (N,N-diphenylcarbamoyl chloride; carbamic chloride, diphenyl-; diphenylcarbamic chloride)

Preparation of diphenylcarbamoyl chloride (N,N-diphenylcarbamoyl chloride; carbamic chloride, diphenyl-; diphenylcarbamic chloride)

In a 5-liter flask are placed 4 liter of benzene and 1690 g of diphenylamine. The flask is cooled in ice and water and 500 g of phosgene passed in. This is determined either by weighing the cylinder from which the phosgene is passing or better by weighing the benzene solution from time to time. This process requires about 3-4 hrs. After all the phosgene has been added, the reaction mixture is allowed to stand 1-2 hours and then the precipitated diphenylamine hydrochloride is filtered. The dark colored benzene solution of diphenylcarbamoyl chloride is distilled until all of the benzene has passed over. The material left in the flask is then poured into 1.5 liters of alcohol. The mixture is cooled thoroly and the diphenylcarbamoyl chloride which precipitates is filtered off and washed with a little alcohol. The material thus prepared is pure and does not need recrystallization. It may be recrystallized from alcohol and melts at about 85 ° C.
The diphenylamine hydrochloride is treated with about 2 liters of hot water which decomposes it and allows the diphenylamine to precipitate as an oil. The mixture is then cooled and the solidified diphenylamine filtered and allowed to dry, after which it is used again for subsequent diphenylcarbamoyl chloride production. There is obtained in this way 953 g of diphenylcarbamoyl chloride (94% yield calculated on diphenylamine not recovered) and 950 g diphenylamine recovered. By repeating the processes described above until practically no diphenylamine is left, a total yield of about 88% of the theory results.

Organic Chemical Reagents, by A. Roger, 65-67, 1919

IUPAC Name

N,N-diphenylcarbamoyl chloride

InChI

InChI=1S/C13H10ClNO/c14-13(16)15(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

InChI Key

XNBKKRFABABBPM-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)N(C2=CC=CC=C2)C(=O)Cl

MeSH Synonyms

diphenylcarbamyl chloride

Depositor-Supplied Synonyms

Diphenylcarbamyl chloride, Diphenylcarbamoyl chloride, 83-01-2, N,N-Diphenylcarbamoyl chloride, Carbamic chloride, diphenyl-, Diphenylcarbamic chloride, N,N-Diphenylcarbamyl chloride, Carbamoyl chloride, diphenyl-, Chloroformic acid diphenylamide, Diphenylchloroformamide, Carabamic chloride, diphenyl-, Carbamic chloride, N,N-diphenyl-, XNBKKRFABABBPM-UHFFFAOYSA-N, NSC 6788, EINECS 201-450-2, AI3-15344, chloro-N,N-diphenylamide, Carbamoyl chloride, diphenyl- (6CI,7CI,8CI), Diphenylcarbamylchloride, AC1Q3GBN, Diphenylcarbamic chloride #, AC1L23VB, KSC353S6F, N,N-diphenyl-carbamoylchloride, SCHEMBL310005, ACMC-20977l, 153591_ALDRICH, UNII-LJ209318B2, 42850_FLUKA, NSC6788, MolPort-002-985-497, BB_SC-7157, NSC-6788, 6089AF, ANW-13615, BBL015755, SBB000709, STK249654, ZINC00119584, AKOS005423326, LJ209318B2, MCULE-9222348217, NE10046, RTR-025897, TRA0079099, AJ-11597, AK-41015, CJ-00870, LS-48815, SC-76643, ZB003988, AB1002241, TR-025897, D0880, ST24046643, ST50308492, EN300-19988, I14-6037, 3B3-022990, InChI=1/C13H10ClNO/c14-13(16)15(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10

Removed Synonyms

CID65741

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