Acetone → HCID 13563677, compound

HRID 979721Notes

Reaction equation

HRID 979721 reaction equation
CC(C)=O.[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1)=[S:21]>O>[CH3:5][N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:20](=[S:21])[O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([CH3:32])([CH3:31])[CH3:33])[CH:24]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 13563671HCID 13563671, compound

Product 1

HCID 13563677HCID 13563677, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 ml of acetone were added 1.07 g of N-methylaniline and 1.38 g of anhydrous potassium carbonate, and a solution obtained by dissolving 2.63 g of O-3-tert-butyl-4-chlorophenyl chlorothioformate into 20 ml of acetone was added thereto with stirring at room temperature. After stirring for 30 minutes as it is, the mixture was subjected to refluxing with heating for 2 hours. The reaction mixture was cooled down to room temperature and then poured into cold water. The product was extracted with benzene. The benzene solution was washed with water and a saturated aqueous solution of sodium chloride in this order, and dried over anhydrous magnesium sulfate. Thereafter, benzene was distilled off. The residue was purified through a column chromatography (employing silica gel as carrier, and benzene/hexane=1/1 (V/V) as developing solvent) and further recrystallized form ethanol to give 2.64 g of O-3-tert-butyl-4-chlorophenyl N-methyl-N-phenylthiocarbamate, having melting point of 65°-67° C.

Workup

  1. customa solution obtained
  2. additionwas added
  3. stirringAfter stirring for 30 minutes as it
  4. temperatureto refluxing
  5. temperaturewith heating for 2 hours
  6. temperatureThe reaction mixture was cooled down to room temperature
  7. extractionThe product was extracted with benzene
  8. washThe benzene solution was washed with water
  9. dry with materiala saturated aqueous solution of sodium chloride in this order, and dried over anhydrous magnesium sulfate
  10. distillationThereafter, benzene was distilled off
  11. customThe residue was purified through a column chromatography (employing silica gel as carrier, and benzene/hexane=1/1 (V/V) as developing solvent) and further recrystallized form ethanol

Sources & evidence

ORD record
ord-f2226b21e55e4c4c80e5532b826bd21a
Source dataset
uspto-grants-1987_05
Patent number
US04668831

Reaction notes

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