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

HRID 1493200Notes

Reaction equation

HRID 1493200 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][CH:15]([F:33])[O:16][C:17]1[CH:32]=[CH:31][C:20]([CH2:21][NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[S:24])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[F:28][C:27]([F:29])([F:30])[CH2:26][N:25]=[C:23]1[N:22]([CH2:21][C:20]2[CH:31]=[CH:32][C:17]([O:16][CH:15]([F:14])[F:33])=[CH:18][CH:19]=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:24]1

Participants

4

Reactant 2

HCID 147741991-(4-Difluoromethoxybenzyl)-3-(2,2,2-trifluoroethyl)thioureaHCID 14801049N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride

Product 1

HCID 147742332-(2,2,2-Trifluoroethylimino)-3(4-difluoromethoxybenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.69 g of N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride and 1.00 g of 1-(4-difluoromethoxybenzyl)-3-(2,2,2-trifluoroethyl)thiourea were dissolved in 30 ml of toluene, and the solution was heated under reflux for 4 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 (10:1)]to give 0.80 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

Sources & evidence

ORD record
ord-10a30a0d8b8a4d33bccf2bcbaaf40c1c
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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