N,N-Dimethylaniline → HCID 18365510, compound

HRID 2418685Notes

Reaction equation

HRID 2418685 reaction equation
CN(C)C1C=CC=CC=1.[C:10]([Cl:13])(Cl)=[O:11].[C:14]1([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C1(C)C(C)=CC=CC=1>[Cl:27][C:23]1[CH:22]=[C:21]([N:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]([Cl:13])=[O:11])[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 6371PhosgeneHCID 75453-Chlorodiphenylamine

Product 1

HCID 18365510HCID 18365510, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 7237O-XyleneSolvent

Procedure

Other of the novel ureas and thioureas of this invention are prepared by reacting arylamines with activated derivatives of carbonic acid such as phosgene or thiophosgene to yield an intermediate, for instance, an arylcarbamyl chloride. This intermediate is then reacted with a secondary amine to yield the urea or thiourea. The preparation of this intermediate is conducted in an aprotic solvent such as toluene or xylene at temperatures from about room temperature up to the boiling point of the solvent in the presence of a base, for example, N,N-dimethylaniline. The intermediate is then reacted with a secondary amine in an aprotic solvent such as toluene at temperatures from room temperature or below up to the boiling point of the solvent. An example of this process is the reaction of phosgene with N-phenyl-3-chloroaniline to yield the intermediate N-(3-chlorophenyl)-N-phenyl carbamyl chloride which is then reacted with N-benzyl-n-butylamine to yield 1-benzyl-1-(n-butyl)-3-(3-chlorophenyl)-3-phenylurea.

Workup

  1. customThe preparation of this intermediate

Sources & evidence

ORD record
ord-3f80ceaa43a24ed4b61eb627576d1488
Source dataset
uspto-grants-1984_09
Patent number
US04473579

Reaction notes

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