Benzoyl chloride → N-(2-Phenylpropan-2-yl)benzamide

HRID 21230

Reaction equation

HRID 21230 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([NH2:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:11][C:10]([NH:19][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68509Cumylamine

Product 1

HCID 13051953N-(2-Phenylpropan-2-yl)benzamideYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 16, benzoyl chloride (10.0 g, 71.1 mmol) was dissolved in dichloromethane (200 mL), and the solution was treated with cumylamine (11.3 mL, 78.3 mmol), triethylamine (14.9 mL, 107 mmol) and DMAP (870 mg, 7.11 mmol), followed by purification by slurry using diisopropylether to obtain N-(1-methyl-1-phenylethyl)benzamide (16.6 g, yield 98%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-89f886efd4ef47dc97a1ac4e120e390a
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

Loading…