4-Chlorobenzoyl chloride → 4-Chloro-N-(3-methyl-2-oxobutyl)benzamide

HRID 485017Notes

Reaction equation

HRID 485017 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[C:12]([CH2:17][NH2:18])(=[O:16])[CH:13]([CH3:15])[CH3:14].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][CH2:17][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 134017361-Amino-3-methylbutan-2-one hydrochloride

Product 1

HCID 134888004-Chloro-N-(3-methyl-2-oxobutyl)benzamideYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.5 g of 4-chlorobenzoyl chloride are added dropwise to a mixture of 4 g of isobutyrylmethylamine hydrochloride, 9.8 g of sodium bicarbonate, 200 ml of ethyl acetate and 100 ml of water at 5° C. to 10° C. under stirring. The mixture is further stirred at room temperature for 3 hours. The ethyl acetate layer is collected, and said layer is washed with water, dried and then condensed under reduced pressure to remove solvent. 6.1 g of N-(4-chlorobenzoyl)isobutyrylmethylamine are obtained. Yield: 87.5%.

Workup

  1. stirringThe mixture is further stirred at room temperature for 3 hours
  2. customThe ethyl acetate layer is collected
  3. washis washed with water
  4. customdried
  5. customcondensed under reduced pressure
  6. customto remove solvent

Sources & evidence

ORD record
ord-bdba2cb030974bcfa469e03c1a481996
Source dataset
uspto-grants-1985_08
Patent number
US04535089

Reaction notes

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