Hydrochloric Acid → N'-{4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}-N,N-dimethylurea

HRID 1679239

Reaction equation

HRID 1679239 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Cl:7][C:8]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.O.Cl>N1C=CC=CC=1>[CH3:1][N:2]([CH3:6])[C:3]([NH:15][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:9]2[CH:18]=[CH:19][C:20]([C:22]([F:23])([F:24])[F:25])=[CH:21][C:8]=2[Cl:7])=[CH:17][CH:16]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 104693274-[2-Chloro-4-(trifluoromethyl)phenoxy]aniline

Product 1

HCID 20362098N'-{4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}-N,N-dimethylureaYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

13 g (0.14 mole) of dimethylcarbamic acid chloride were added dropwise to 29 g (0.1 mole) of 4-(2-chloro-4-trifluoromethyl-phenoxy)-aniline, dissolved in 50 ml of pyridine, at 0° C. The mixture was warmed to 70°-75° C for half an hour, the bulk of the pyridine was stripped off in vacuo and the residue was poured into water and acidified with dilute hydrochloric acid. The precipitate was filtered off, dried and recrystallized from toluene. 29 g (89% of theory) of N,N-dimethyl-N'-[4-(2-chloro-4-trifluoromethylphenoxy)-phenyl]-urea were obtained as pink crystals of melting point 140° C.

Workup

  1. temperatureThe mixture was warmed to 70°-75° C for half an hour
  2. filtrationThe precipitate was filtered off
  3. customdried
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-5c3a23b6e3d148508c71b1315686de45
Source dataset
uspto-grants-1978_03
Patent number
US04080193

Linked notes

Loading…