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912368-67-3

912368-67-3 Structure

912368-67-3 Structure
IdentificationBack Directory
[Name]

3-cyano-3-(2-thienyl)acrylic acid potassium salt
[CAS]

912368-67-3
[Synonyms]

POTASSIUM 3-CYANO-3-(THIOPHEN-2-YL)ACRYLATE
Potassium (Z)-3-cyano-3-(thiophen-2-yl)acrylate
3-cyano-3-(2-thienyl)acrylic acid potassium salt
2-Propenoic acid,3-cyano-3-(2-thienyl)-,potassium salt,(2Z)-
[Molecular Formula]

C8H6KNO2S
[MDL Number]

MFCD29924754
[MOL File]

912368-67-3.mol
[Molecular Weight]

219.3
Chemical PropertiesBack Directory
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
Hazard InformationBack Directory
[Synthesis]

2-Thiopheneacetonitrile

20893-30-5

Glyoxylic acid

298-12-4

3-cyano-3-(2-thienyl)acrylic acid potassium salt

912368-67-3

General Steps: Step 1: Synthesis of potassium (Z)-3-cyano-3-(thiophen-2-yl)acrylate To a stirred solution of 2-thiophene acetonitrile (24.8 g, 0.20 mol) in methanol (300 mL) was sequentially added glyoxalate monohydrate (18.5 g, 0.20 mol) and potassium carbonate (25.5 g, 0.20 mol). The reaction mixture was heated to reflux under nitrogen protection. After 2 h of reaction, it was cooled to room temperature and the product was collected by filtration. The filter cake was washed with a large amount of methanol and subsequently dried overnight in a vacuum oven to afford 43.1 g (99% yield) of the target product, potassium (Z)-3-cyano-3-(thiophen-2-yl)acrylate, as a white crystalline potassium salt. Product characterization data: 1H NMR (δ, ppm): 7.95 (d, 3H), 7.75 (d, 1H), 7.30 (dd, 1H), 7.05 (s, 1H), 3.0-4.0 (br s, 1H). LCMS (ES): m/z 180 [M+H]+, m/z 78 [M-H]-.

[References]

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1061 - 1073
[2] Patent: WO2006/106326, 2006, A1. Location in patent: Page/Page column 53
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