Acetonitrile → HCID 71293687, compound

HRID 2410234Notes

Reaction equation

HRID 2410234 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]=1N.C(#[N:26])C>>[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[N: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])[C:14]([NH2:26])=[O:15]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 95842-FluoroanilineHCID 11983909Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)-

Product 1

HCID 71293687HCID 71293687, compound

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

  1. washthe mixture is rinsed in with acetonitrile (50 ml)
  2. customseeded at ca. 78° C.
  3. stirringstirred for ca. 15 min
  4. temperatureThe suspension is cooled to 0° C.
  5. filtrationthe product is filtered off with suction
  6. washwashed with acetonitrile (950 ml, cooled to 0-5° C.)
  7. customThe product is dried overnight at 45° C. in a vacuum
  8. customdrying oven

Sources & evidence

ORD record
ord-f6c4e559c0414f11a66cab9eb9efbb6f
Source dataset
uspto-grants-2014_08
Patent number
US08816075B2

Reaction notes

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