1-(4-t-Butoxycarbonylbenzyl)-3-(2,2,2-trifluoroethyl)thiourea → 2-(2,2,2-Trifluoroethylimino)-3-(4-t-butoxycarbonylbenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

HRID 1493202Notes

Reaction equation

HRID 1493202 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].[C:14]([O:18][C:19]([C:21]1[CH:36]=[CH:35][C:24]([CH2:25][NH:26][C:27]([NH:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[S:28])=[CH:23][CH:22]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>C1C=CC=CC=1>[F:32][C:31]([F:33])([F:34])[CH2:30][N:29]=[C:27]1[N:26]([CH2:25][C:24]2[CH:35]=[CH:36][C:21]([C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:20])=[CH:22][CH:23]=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:28]1

Participants

4

Reactant 2

HCID 147742081-(4-t-Butoxycarbonylbenzyl)-3-(2,2,2-trifluoroethyl)thioureaHCID 14801049N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride

Product 1

HCID 147742502-(2,2,2-Trifluoroethylimino)-3-(4-t-butoxycarbonylbenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 49%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

0.31 g of N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride and 0.49 g of 1-(4-t-butoxycarbonylbenzyl)-3-(2,2,2-trifluoroethyl)thiourea were dissolved in 30 ml of benzene, and the solution was heated under reflux for 5 hours. After the reaction, benzene was evaporated under reduced pressure. The resulting oily product was purified by column chromatography [silica gel; developing solvent hexane/ethyl acetate (9:1)) to obtain 0.34 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-f33484f52b694ffd835f4f04eccbac1a
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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