1-Butanol → HCID 59179697, compound

HRID 2381859Notes

Reaction equation

HRID 2381859 reaction equation
[C:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:13])[CH:4]=1)#[N:2].[C:14]1([CH2:20][C:21]([NH:23][NH2:24])=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](O)[CH2:32]CC>>[CH2:20]([C:21]1[NH:23][N:24]=[C:1]([C:3]2[S:7][C:6]([C:8]([O:10][CH2:11][CH2:12][CH2:31][CH3:32])=[O:9])=[C:5]([CH3:13])[CH:4]=2)[N:2]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 11430Potassium CarbonateHCID 70301Benzeneacetic acid, hydrazideHCID 591796841034981-21-9

Product 1

HCID 59179697HCID 59179697, compoundYield 42%

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 5-cyano-3-methylthiophene-2-carboxylate (0.37 g, 1.90 mmol), phenylacetic hydrazide (0.29 g, 1.90 mmol) and potassium carbonate (0.26 g, 1.90 mmol) in 1-butanol (5 mL) was stirred in a sealed tube at 150° C. for 20 h. The reaction mixture was cooled to ambient temperature and concentrated. The residue was purified by column chromatography eluted with 0-30% ethyl acetate in hexanes to afford the title compound as a colorless solid (0.28 g, 42%). 1H NMR (300 MHz, CDCl3) δ 10.49 (br s, 1H), 7.46 (s, 1H), 7.41-7.27 (m, 5H), 4.28 (t, J=6.5 Hz, 2H), 4.21 (s, 2H), 2.56 (s, 3H), 1.77-1.66 (m, 2H), 1.54-1.40 (m, 2H), 0.96 (t, J=7.3 Hz, 3H); MS (ES+) m/z 356.3 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography
  4. washeluted with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b56acce462074d2aa3df509cda3dcef5
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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