Aniline → Ethyl 1-(phenylaminocarbonyl)cyclopropanecarboxylate

HRID 486997Notes

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.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>>[C:19]1([NH:18][C:9]([C:6]2([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][CH2:8]2)=[O:11])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 4

HCID 6115Aniline

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Product 1

HCID 14150218Ethyl 1-(phenylaminocarbonyl)cyclopropanecarboxylate

Procedure

1-Carboethoxycyclopropanecarboxylic acid (3.95 grams, 0.025 mole), ethyl chloroformate (2.71 grams, 0.025 mole) and aniline (2.33 grams, 0.025 mole) were reacted sequentially in the presence of triethylamine (2.53 grams, 0.025 mole) in a manner similar to that described for ethyl 1-(4-chloro-2-ethylphenylamlnocarbonyl)cyclopropanecarboxylate in Example XXXIII to give ethyl 1-(phenylaminocarbonyl)cyclopropanecarboxylate which was then hydrolyzed in a manner similar to that described in Example VII to give 2.42 grams (0.01 mole) of 1-(phenylaminocarbonyl)cyclopropanecarboxylic acid having a melting point of 178° C.-181° C. NMR analysis of the product indicated the following:

Sources & evidence

ORD record: ord-db912c6e14654573865fc967531252f1
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292937

Reaction notes

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