1-Chloro-2-(isocyanatomethyl)benzene → N-(2-Hydroxy-4-cyanophenyl)N'-(2-chlorobenzyl)urea

HRID 650103

Reaction equation

HRID 650103 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[C:6]=[O:7].[OH:12][C:13]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:14]=1[NH2:15]>CN(C=O)C>[OH:12][C:13]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:14]=1[NH:15][C:6]([NH:5][CH2:4][C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[Cl:1])=[O:7]

Participants

4

Reactant 2

HCID 27333671-Chloro-2-(isocyanatomethyl)benzeneHCID 101977194-Amino-3-hydroxybenzonitrile

Product 1

HCID 21714412N-(2-Hydroxy-4-cyanophenyl)N'-(2-chlorobenzyl)ureaYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chlorobenzylisocyanate (125.6 mg, 0.75 mmol) in DMF (1.0 ml), 2-hydroxy-4-cyanoaniline (100 mg, 0.75 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (80 mg, 58.8%). EI-MS m/z 302.8 (M+).

Sources & evidence

ORD record
ord-a28e45464f8b4e359c7ab98f98b4f3f1
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Linked notes

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