Triethylamine → HCID 19096813, compound

HRID 486996Notes

Reaction equation

[C:1]([C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].ClC(OCC)=O.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([NH:23][CH3:24])=[CH:21][CH:20]=1.C(N(CC)CC)C>>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([N:23]([CH3:24])[C:9]([C:6]2([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][CH2:8]2)=[O:11])=[CH:21][CH:20]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

HCID 702724-Chloro-N-methylbenzenamine

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Product 1

HCID 19096813HCID 19096813, compoundYield 22.9%

Procedure

1-Carboethoxycyclopropanecarboxylic acid (5.54 grams, 0.035 mole), ethyl chloroformate (3.80 grams, 0.035 mole) and 4-chloro-N-methylaniline (4.96 grams, 0.035 mole) were reacted sequentially in the presence of triethylamine (3.54 grams, 0.035 mole) in a manner similar to that described in Example XXXIII to give 2.26 grams (0.008 mole) of ethyl 1-[N-(4-chlorophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate having a melting point of 53° C.-56.5° C. NMR analysis of the product indicated the following:

Sources & evidence

ORD record: ord-de0a019131954493b17579d634df0d60
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292937

Reaction notes

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