N,N-Dimethylaniline → HCID 20448947, compound

HRID 2166523Notes

Reaction equation

HRID 2166523 reaction equation
CN(C)C1C=CC=CC=1.[C:10]([Cl:13])(Cl)=[O:11].[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>C1(C)C=CC=CC=1.C1(C)C(C)=CC=CC=1>[Cl:14][C:15]1[CH:16]=[C:17]([NH:18][C:10]([Cl:13])=[O:11])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 6371PhosgeneHCID 79323-Chloroaniline

Product 1

HCID 20448947HCID 20448947, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 7237O-XyleneSolvent

Procedure

Other of the 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 3-chloroaniline to yield the intermediate N-(3-chlorophenyl)carbamyl chloride which is then reacted with di-(n-butyl)amine to yield 1,1-di-(n-butyl)-3-(3-chlorophenyl)urea.

Workup

  1. customThe preparation of this intermediate

Sources & evidence

ORD record
ord-b1ce713a18574542a6656d99786b5173
Source dataset
uspto-grants-1983_06
Patent number
US04387105

Reaction notes

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