2,4-Difluoroaniline → phenyl N-(2,4-difluorophenyl)carbamate

HRID 359973Notes

Reaction equation

HRID 359973 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:11](=[O:12])[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 15891Phenyl chloroformate

Product 1

HCID 13733129phenyl N-(2,4-difluorophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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 2,4-difluoroaniline with phenyl chloroformate to yield the intermediate phenyl N-(2,4-difluorophenyl)carbamate which is then reacted with N-(4-butylphenyl)-N-(6-hydroxyhexyl)amine to yield 1-(4-n-butylphenyl)-3-(2,4-difluorophenyl)-1-(6-hydroxyhexyl)urea.

Sources & evidence

ORD record
ord-52497e92dcd04dc7acd0f11e34b8a251
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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