Potassium Carbonate → 2-Methylimino-3-methyl-5-benzyl-tetrahydro-1,3,5-thiadiazin-4-one

HRID 237074Notes

Reaction equation

HRID 237074 reaction equation
[CH2:1]([N:8]([CH2:12]Cl)[C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][NH:15][C:16]([NH:18][CH3:19])=[S:17].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:14][N:15]=[C:16]1[N:18]([CH3:19])[C:9](=[O:10])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][S:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723631N,N'-DimethylthioureaHCID 21314706N-benzyl-N-chloromethylcarbamoyl chloride

Product 1

HCID 213147022-Methylimino-3-methyl-5-benzyl-tetrahydro-1,3,5-thiadiazin-4-oneYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.4 g (0.02 mole) of N-benzyl-N-chloromethylcarbamoyl chloride and 2.0 g (0.02 mole) of 1,3-dimethylthiourea was dissolved in 50 ml of ethyl alcohol and heated under reflux with stirring for 2 hours. After addition of 20 ml of a saturated aqueous potassium carbonate solution, the mixture was extracted with 100 ml of benzene. The benzene layer was washed with water, dried, and freed from the benzene by distillation under reduced pressure to obtain 4.0 g of crude crystals which were recrystallized from ether. Yield 3.2 g (63%); m.p. 93°-95° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. extractionthe mixture was extracted with 100 ml of benzene
  4. washThe benzene layer was washed with water
  5. customdried
  6. distillationfreed from the benzene by distillation under reduced pressure

Sources & evidence

ORD record
ord-7ce92d3519144c1d8a85ec3ce9a8d49e
Source dataset
uspto-grants-1979_06
Patent number
US04159328

Reaction notes

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