Water → N-{3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-N'-methylurea

HRID 1679240Notes

Reaction equation

HRID 1679240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)[NH2:5].[CH3:20][N:21]=[C:22]=[O:23].O>C(#N)C.C(N(CC)CC)C>[CH3:20][NH:21][C:22]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)=[C:2]([Cl:1])[CH:3]=1)=[O:23]

Participants

6

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]aniline

Product 1

HCID 20362100N-{3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-N'-methylureaYield 29%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

18.7 g (0.06 mole) of 3-chloro-4-(3-trifluoromethylphenoxy)-aniline were dissolved in 100 ml of acetonitrile, and 3 drops of triethylamine and 4.3 g (0.078 mole) of methylisocyanate were added at 10° C. The mixture was stirred for a further 4 hours at room temperature and then poured into water, and when the reaction mixture had crystallized throughout the solid was filtered off and recrystallized from toluene. 6 g (29% of theory) of N-methyl-N'-[3-chloro-4-(3-trifluoromethylphenoxy)-phenyl]-urea of melting point 160° C were obtained.

Workup

  1. customhad crystallized throughout the solid
  2. filtrationwas filtered off
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e69580adc9fb46aea63300aab384717d
Source dataset
uspto-grants-1978_03
Patent number
US04080193

Reaction notes

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