4-Chloro-3-(trifluoromethyl)aniline → Ethyl 4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)benzoate

HRID 78330

Reaction equation

HRID 78330 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)=[C:2]=[O:3].[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24]>C(Cl)Cl>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:2]([NH:1][C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=2)=[O:3])=[CH:18][C:17]=1[C:23]([F:24])([F:25])[F:26]

Participants

4

Reactant 2

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 2212218Ethyl 4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)benzoateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 4-isocyanatobenzoate (3.14 g, 16.4 mmol) in CH2Cl2 (30 mL) was added 4-chloro-3-(trifluoromethyl)aniline (3.21 g, 16.4 mmol), and the solution was stirred at room temp. overnight. The resulting slurry was diluted with CH2Cl2 (50 mL) and filtered to afford N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(4-ethoxycarbonylphenyl)urea as a white solid (5.93 g, 97%): TLC (40% EtOAc/60% hexane) Rf 0.44.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-99b39eae20d145379a672358c08bdaf8
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Linked notes

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