Ethanol → 2-[1-(5-Cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl ester

HRID 1836652Notes

Reaction equation

HRID 1836652 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9](=O)[C:10]1[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=1[F:18])=[O:5])[CH3:2].[C:20]1([CH3:31])[CH:25]=[CH:24][C:23]([S:26]([NH:29]N)(=[O:28])=[O:27])=[CH:22][CH:21]=1.[CH2:32](O)C>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]([C:10]1[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=1[F:18])=[CH:32][NH:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:31])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 15303P-ToluenesulfonylhydrazideHCID 698411172-(5-Cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 698401482-[1-(5-Cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl esterYield 66%

Procedure

2-(5-cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester (1.62 g, 6.2 mmol) and p-toluenesulfonhydrazide (2.31 g, 12.4 mmol) were refluxed in 50 mL ethanol for 36 h. The reaction was concentrated in vacuo, then purified by flash chromatography on silica gel using ethyl acetate/hexane (0-25%) as the eluent to give 2-[1-(5-cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl ester (1.77 g, 66%) as a mixture of cis and trans isomers. 1H NMR (500 MHz, CDCl3) 7.87 (1H, d, J=8.24 Hz), 7.78 (0.5H, m), 7.76 (1H, d, J=8.24 Hz), 7.65 (0.5H, m), 7.61 (0.5H, dd, J 2.14, 6.71 Hz), 7.44 (0.5H, dd, J=2.14, 5.80 Hz), 7.36 (2H, dd, J=3.96, 7.93 Hz), 7.31 (0.5H, t, J=8.54 Hz), 7.18 (0.5H, t, J=8.54 Hz), 4.22 (1H, m), 4.12 (2H, dq, J=7.32, 4.27 Hz), 2.46 (3H, 2s), 2.20 (0.5H, m), 1.99 (0.5H, m), 1.66 (0.5H, mn), 1.43 (0.5H, m), 1.31 (2H, m), 1.27 (3H, dt, J=7.02, 3.67 Hz). MS m/e 430.13 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4056820a37f6444d82b5f052875be4ef
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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