2-Fluoro-5-methylphenyl isocyanate → N-(4-bromo-2-ethylphenyl)-N'-(2-fluoro-5-methylphenyl)urea

HRID 239882

Reaction equation

HRID 239882 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[N:19]=[C:20]=[O:21]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20]([NH:19][C:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=2[F:11])=[O:21])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 27333772-Fluoro-5-methylphenyl isocyanateHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 66680634N-(4-bromo-2-ethylphenyl)-N'-(2-fluoro-5-methylphenyl)ureaYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2-ethylaniline (200 mg) in dichloromethane (10 mL) was treated with 1-fluoro-2-isocyanato-4-methylbenzene (151 mg), stirred at room temperature overnight, diluted with hexanes, and filtered. The filter cake provided 227 mg of the desired product. MS (ESI(+)) m/e 351,353 (M+H)+.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-2b6b93845cc1458e9aa075848bbde5c7
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Linked notes

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