2-Chlorobenzoyl chloride → Ethyl 2-(2-chlorobenzoyl)-3-dimethylaminopropenoate

HRID 1170451Notes

Reaction equation

HRID 1170451 reaction equation
CN[C:3]([NH:10][CH3:11])=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:12](N(CC)C(C)C)(C)C.[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C1(C)C=CC=CC=1>[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](=[O:25])[C:4](=[CH:3][N:10]([CH3:11])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 85819813Ethyl 3,3-dimethylaminoacrylate

Product 1

HCID 54509863Ethyl 2-(2-chlorobenzoyl)-3-dimethylaminopropenoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3,3-dimethylaminoacrylate (4.68 g, 32.7 mmol) and N,N-diisopropylethylamine (12 mL, 8.9 g, 69 mmol) was stirred at rt and a solution of 2-chlorobenzoyl chloride (5.72 g, 32.7 mmol) in 30 mL of toluene was added over 5 mins.

Sources & evidence

ORD record
ord-48fe0e069c824971aa6c0af41ecb916f
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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