Acetone → HCID 13656344, compound

HRID 979719Notes

Reaction equation

HRID 979719 reaction equation
CC(C)=O.[Cl:5][C:6]1[CH:7]=[C:8]([N:12]([CH3:16])[C:13](Cl)=[O:14])[CH:9]=[CH:10][CH:11]=1.[C:17]([C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[CH:25][C:26]=1[Cl:27])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:5][C:6]1[CH:7]=[C:8]([N:12]([CH3:16])[C:13](=[O:14])[O:28][C:23]2[CH:24]=[CH:25][C:26]([Cl:27])=[C:21]([C:17]([CH3:20])([CH3:18])[CH3:19])[CH:22]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 10910230HCID 10910230, compoundHCID 13882387HCID 13882387, compound

Product 1

HCID 13656344HCID 13656344, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of acetone were added 2.04 g of N-(3-chlorophenyl)-N-methylcarbamoyl chloride, 1.84 g of 3-tert-butyl-4-chlorophenol and 1.6 g of anhydrous potassium carbonate, and the mixture was refluxed with heating for 48 hours. The reaction mixture was cooled down to room temperature and thereafter was 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 was dried over anhydrous magnesium sulfate. Thereafter, benzene was distilled off. The residue was purified through a column chromatography (employing silica gel as carrier and benzen as developing solvent), and further recrystallized from hexane to give 3.2 g of 3-tert-butyl-4-chlorophenyl N-(3-chlorophenyl)-N-methylcarbamate, having melting point of 65°-67° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 48 hours
  3. extractionThe product was extracted with benzene
  4. washThe benzene solution was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride in this order, and was dried over anhydrous magnesium sulfate
  6. distillationThereafter, benzene was distilled off
  7. customThe residue was purified through a column chromatography (employing silica gel as carrier and benzen as developing solvent)
  8. customfurther recrystallized from hexane

Sources & evidence

ORD record
ord-c62ccf94b4cd4514b1669a2aa44d13c7
Source dataset
uspto-grants-1987_05
Patent number
US04668831

Reaction notes

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