1-(4-Trifluoromethylbenzyl)-3-(2,2,2-trifluoroethyl)thiourea → 2-(2,2,2-Trifluoroethylimino)-3-(4-trifluoromethylbenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

HRID 1493197Notes

Reaction equation

HRID 1493197 reaction equation
Cl[CH2:2][N:3]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[C:4](Cl)=[O:5].[F:14][C:15]([F:33])([F:32])[C:16]1[CH:31]=[CH:30][C:19]([CH2:20][NH:21][C:22]([NH:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[S:23])=[CH:18][CH:17]=1>C1C=CC=CC=1>[F:27][C:26]([F:28])([F:29])[CH2:25][N:24]=[C:22]1[N:21]([CH2:20][C:19]2[CH:30]=[CH:31][C:16]([C:15]([F:33])([F:14])[F:32])=[CH:17][CH:18]=2)[C:4](=[O:5])[N:3]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH2:2][S:23]1

Participants

4

Reactant 2

HCID 148010421-(4-Trifluoromethylbenzyl)-3-(2,2,2-trifluoroethyl)thioureaHCID 14801049N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride

Product 1

HCID 148010502-(2,2,2-Trifluoroethylimino)-3-(4-trifluoromethylbenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1.00 g of N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride and 1.45 g of 1-(4-trifluoromethylbenzyl)-3-(2,2,2-trifluoroethyl)thiourea were dissolved in 30 ml of benzene, and the solution was heated under reflux for 4 hours. After the reaction, benzene was evaporated under reduced pressure. The resulting oily product was purified by column chromatography [silica gel; eluent: hexane/ethyl acetate (10/1)] to give 1.27 g of the captioned compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. customwas evaporated under reduced pressure
  4. customThe resulting oily product was purified by column chromatography [silica gel; eluent: hexane/ethyl acetate (10/1)]

Sources & evidence

ORD record
ord-97e0b803965f4a9b93f9d8386d1bf1ca
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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