N-(2,2,2-Trifluoroethyl)-N′-[[4-(trifluoromethoxy)phenyl]methyl]thiourea → HCID 14774259, compound

HRID 1493203Notes

Reaction equation

HRID 1493203 reaction equation
Cl[CH2:2][N:3]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[F:14])[C:4](Cl)=[O:5].[F:15][C:16]([F:35])([F:34])[O:17][C:18]1[CH:33]=[CH:32][C:21]([CH2:22][NH:23][C:24]([NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[S:25])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[F:29][C:28]([F:30])([F:31])[CH2:27][N:26]=[C:24]1[N:23]([CH2:22][C:21]2[CH:20]=[CH:19][C:18]([O:17][C:16]([F:35])([F:15])[F:34])=[CH:33][CH:32]=2)[C:4](=[O:5])[N:3]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=2[F:14])[CH2:2][S:25]1

Participants

4

Reactant 2

HCID 14774180N-(2,2,2-Trifluoroethyl)-N′-[[4-(trifluoromethoxy)phenyl]methyl]thioureaHCID 19830703HCID 19830703, compound

Product 1

HCID 14774259HCID 14774259, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.60 g of N-chloromethyl-N-(2-fluoro-4-methylphenyl)carbamoyl chloride and 0.84 g of 1-(4-trifluoromethoxybenzyl)-3-(2,2,2-trifluoroethyl)thiourea were dissolved in 50 ml of toluene, and the solution was heated under reflux for 5 hours. After the reaction, toluene was evaporated under reduced pressure. The resulting oily product was purified by column chromatography silica gel; developing solvent hexane/ethyl acetate (9:1)) to give 0.68 g of the captioned compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 5 hours
  3. customwas evaporated under reduced pressure
  4. customThe resulting oily product was purified by column chromatography silica gel

Sources & evidence

ORD record
ord-499244848d4b4c3b81d4d41457622a6c
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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