4-Chloro-3-(trifluoromethyl)aniline → HCID 23276663, compound

HRID 2083392Notes

Reaction equation

HRID 2083392 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])=[O:8])=[CH:17][C:16]=1[C:22]([F:23])([F:24])[F:25]

Participants

4

Reactant 2

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 27333692,6-Difluorobenzoyl isocyanate

Product 1

HCID 23276663HCID 23276663, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 9.2 g (0.05 mole) of 2,6-difluorobenzoylisocyanate in 50 ml of toluene was added dropwise at 40° C to a solution of 9.8 g (0.05 mole) of 4-chloro-3-trifluoromethylaniline in 100 ml of toluene. The batch was stirred for 1 hour at 40° C. The substance which separated out was filtered off after cooling the reaction mixture to 20° C, and washed with toluene and petroleum ether. After drying, 18.0 g (95% of theory) of N-(4-chloro-3-trifluoromethylphenyl)-N'-(2,6-difluorobenzoyl)-urea of melting point 220° C were obtained.

Workup

  1. customThe substance which separated out
  2. filtrationwas filtered off
  3. temperatureafter cooling the reaction mixture to 20° C
  4. washwashed with toluene and petroleum ether
  5. customAfter drying

Sources & evidence

ORD record
ord-b49ef3f8b1d84e1a94adf88d3eb7db16
Source dataset
uspto-grants-1978_04
Patent number
US04085226

Reaction notes

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