Aniline → Ethyl 1-(phenylaminocarbonyl)cyclopropanecarboxylate

HRID 893207Notes

Reaction equation

C(C1(C(O)=O)CC1)(OCC)=O.ClC(OCC)=O.NC1C=CC=CC=1.C(N(CC)CC)C.Cl[C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([C:42]2([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:44][CH2:43]2)=[O:41])=[C:35](CC)[CH:34]=1>>[C:36]1([NH:39][C:40]([C:42]2([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:43][CH2:44]2)=[O:41])[CH:35]=[CH:34][CH:33]=[CH:38][CH:37]=1

Participants

Reactant 5

HCID 6115Aniline

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

HCID 19096849Ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate

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-ethylphenylaminocarbonyl)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-2cda3b49a0244928a99782c62d43e892
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05123951

Reaction notes

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