Water → 3-chloro-N-(1-methyl-1-phenylethyl)benzamide

HRID 21005

Reaction equation

HRID 21005 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]([NH2:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[CH3:12].C(N(CC)CC)C.O>ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:20][C:11]([CH3:13])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 68509CumylamineHCID 69252Benzoyl chloride, 3-chloro-

Product 1

HCID 474447613-chloro-N-(1-methyl-1-phenylethyl)benzamideYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoylchloride (110.0 g, 57.1 mmol) was dissolved in dichloromethane (200 mL), and the solution was added with cumylamine (9.04 mL, 62.9 mmol), triethylamine (12.0 mL, 85.7 mmol) and DMAP (698 mg, 5.71 mmol), followed by stirring at room temperature for 3 hours. The reaction mixture was added with water, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using diisopropyl ether to obtain 3-chloro-N-(1-methyl-1-phenylethyl)benzamide (15.0 g, yield 96%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by slurry

Sources & evidence

ORD record
ord-95cd312236934178bc6fff74326d23f0
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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