Triethylamine → 3,4-dichloro-N-(1-methyl-1-phenylethyl)benzamide

HRID 21234

Reaction equation

HRID 21234 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[C:12]([NH2:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:21][C:12]([CH3:14])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 76403Benzoyl chloride, 3,4-dichloro-

Product 1

HCID 130519573,4-dichloro-N-(1-methyl-1-phenylethyl)benzamideYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 16, 3,4-dichlorobenzoyl chloride (3.00 g, 14.3 mmol) was dissolved in dichloromethane (60 mL), and the solution was treated with cumylamine (2.30 mL, 15.7 mmol), triethylamine (3.00 mL, 21.5 mmol) and DMAP (175 mg, 1.43 mmol), followed by purification by slurry using chloroform to obtain 3,4-dichloro-N-(1-methyl-1-phenylethyl)benzamide (3.85 g, yield 88%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-392a4fb00f8148fe8cea8dc5b9d046b0
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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