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

HRID 1493201Notes

Reaction equation

HRID 1493201 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:36])([C:20]1[CH:35]=[CH:34][C:23]([CH2:24][NH:25][C:26]([NH:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[S:27])=[CH:22][CH:21]=1)[C:16]([F:19])([F:18])[F:17]>C1(C)C=CC=CC=1>[F:31][C:30]([F:32])([F:33])[CH2:29][N:28]=[C:26]1[N:25]([CH2:24][C:23]2[CH:22]=[CH:21][C:20]([C:15]([F:14])([F:36])[C:16]([F:17])([F:18])[F:19])=[CH:35][CH:34]=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:27]1

Participants

4

Reactant 2

HCID 147741971-(4-Pentafluoroethylbenzyl)-3-(2,2,2-trifluoroethyl)thioureaHCID 14801049N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride

Product 1

HCID 147742482-(2,2,2-Trifluoroethylimino)-3-(4-pentafluoroethylbenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 43.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.71 g of N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride and 1.20 g of 1-(4-pentafluoroethylbenzyl)-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 0.72 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-c5759abc1cb749cdad948b44d67a4bcb
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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