2-Fluoroaniline → N-(2-fluorophenyl)-N'-[2-methoxy-5-(trifluoromethyl)phenyl]urea
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N:13]=[C:14]=[O:15].[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>C(#N)C>[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][C:14]([NH:13][C:4]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 82 °C
Procedure
2-Methoxy-5-trifluoromethylphenyl isocyanate (1057.8 g) is dissolved in acetonitrile (4240 ml), then 2-fluoroaniline (540.8 g) is added thereto and the mixture is rinsed in with acetonitrile (50 ml). The resulting clear solution is stirred under reflux (ca. 82° C.) for 4 h, then seeded at ca. 78° C. and stirred for ca. 15 min. The suspension is cooled to 0° C., and the product is filtered off with suction and washed with acetonitrile (950 ml, cooled to 0-5° C.). The product is dried overnight at 45° C. in a vacuum drying oven using entraining nitrogen. A total of 1380.8 g of N-(2-fluorophenyl)-N′-[2-methoxy-5-(trifluoromethyl)phenyl]urea are obtained as a solid, corresponding to 86.4% of theory.
Workup
- washthe mixture is rinsed in with acetonitrile (50 ml)
- customseeded at ca. 78° C.
- stirringstirred for ca. 15 min
- temperatureThe suspension is cooled to 0° C.
- filtrationthe product is filtered off with suction
- washwashed with acetonitrile (950 ml, cooled to 0-5° C.)
- customThe product is dried overnight at 45° C. in a vacuum
- customdrying oven
Sources & evidence
- ORD record
- ord-1f27c18efdb343a386945689983bf5f3
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372972B2
Reaction notes
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