Triethylamine → ethyl 1-[N-(4-bromophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate

Reaction equation

Cl[C:2]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)=[O:3].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([NH:17][CH3:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([N:17]([CH3:18])[C:2]([C:4]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]2)=[O:3])=[CH:15][CH:14]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 2757052Benzenamine, 4-bromo-N-methyl-

HCID 14233946Ethyl 1-chlorocarbonylcyclopropanecarboxylate

Product 1

HCID 19096870ethyl 1-[N-(4-bromophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylateYield 50%

Procedure

Ethyl 1-chlorocarbonylcyclopropanecarboxylate (3.11 grams, 0.02 mole), prepared in Example XVIII, 4-bromo-N-methylaniline (3.00 grams, 0.02 mole) and triethylamine (1.63 grams, 0.02 mole) were reacted in a manner similar to that described in Example III to give 3.79 grams (0.01 mole) of ethyl 1-[N-(4-bromophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate isolated as a colorless oil. Elemental analysis of the product indicated the following: