Acetone → HCID 13656345, compound

HRID 979723Notes

Reaction equation

HRID 979723 reaction equation
CC(C)=O.[F:5][C:6]1[CH:13]=[CH:12][C:9]([NH:10][CH3:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=1)=[O:22]>O>[F:5][C:6]1[CH:13]=[CH:12][C:9]([N:10]([CH3:11])[C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 11430Potassium CarbonateHCID 680244-Fluoro-N-methylanilineHCID 13656356HCID 13656356, compound

Product 1

HCID 13656345HCID 13656345, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 ml of acetone were added 1.25 g of 4-fluoro-N-methylaniline and 1.38 g of anhydrous potassium carbonate, and a solution obtained by dissolving 2.5 g of 3-tert-butyl-4-chlorophenyl chloroformate into 20 ml of acetone was added thereto with stirring at room temperature. After stirring for 30 minutes as it is, the mixture was refluxed with heating for 2 hours. After cooled down to room temperature, the reaction mixture was poured into cold water and the resultant product was extracted with benzene. The benzene solution was washed with water and a saturated aqueous solution of sodium chloride in this order, dried over anhydrous magnesium sulfate, and thereafter benzene was distilled off under reduced pressure. The residue was purified through a column chromatography (employing silica gel as carrier and benzene as developing solvent) and further recrystallized from ethanol to give 2.7 g of 3-tert-butyl-4-chlorophenyl N-(4-fluorophenyl)-N-methylcarbamate having melting point of 92°-94° C.

Workup

  1. customa solution obtained
  2. additionwas added
  3. stirringAfter stirring for 30 minutes as it
  4. temperaturethe mixture was refluxed
  5. temperaturewith heating for 2 hours
  6. temperatureAfter cooled down to room temperature
  7. extractionthe resultant 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, dried over anhydrous magnesium sulfate
  10. distillationbenzene was distilled off under reduced pressure
  11. customThe residue was purified through a column chromatography (employing silica gel as carrier and benzene as developing solvent)
  12. customfurther recrystallized from ethanol

Sources & evidence

ORD record
ord-a72148b30eca4329ac022962c6fba810
Source dataset
uspto-grants-1987_05
Patent number
US04668831

Reaction notes

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