N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride → 2-(2,2,2-Trifluoroethylimino)-3-(4-isopropyloxybenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

HRID 1493198Notes

Reaction equation

HRID 1493198 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].[CH:14]([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)([CH3:16])[CH3:15]>C1C=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:32]=[CH:33][C:18]([O:17][CH:14]([CH3:16])[CH3:15])=[CH:19][CH:20]=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:25]1

Participants

4

Reactant 2

HCID 14801049N-chloromethyl-N-(4-methylphenyl)carbamoyl chlorideHCID 198306931-(4-Isopropyloxybenzyl)-3-(2,2,2-trifluoroethyl)thiourea

Product 1

HCID 148010652-(2,2,2-Trifluoroethylimino)-3-(4-isopropyloxybenzyl)-5-(4-methylphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 36.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1.00 g of N-chloromethyl-N-(4-methylphenyl)carbamoyl chloride and 1.40 g of 1-(4-isopropyloxybenzyl)-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)1 to give 0.75 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-94e1250b4416416aaad6e1ac1f455bfe
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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