Dimethyl Sulfoxide → 2-(5-Methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile

HRID 1355907Notes

Reaction equation

HRID 1355907 reaction equation
[P].[S].[CH3:3][C:4]1[O:8][C:7]([C:9](=[O:13])[CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[H-].[Na+].[C:16](=S)=[S:17].CI.[CH3:21][S:22]([CH3:24])=O>>[CH3:3][C:4]1[O:8][C:7]([C:9]([C:10](=[C:21]([S:17][CH3:16])[S:22][CH3:24])[C:11]#[N:12])=[O:13])=[CH:6][CH:5]=1

Participants

8

Reactant 7

HCID 679Dimethyl Sulfoxide2×HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 5362487SulfurHCID 5462309PhosphorusHCID 153240603-(5-Methylfuran-2-yl)-3-oxopropanenitrile

Product 1

HCID 865837512-(5-Methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrileYield 89%

Procedure

Following the method of Rudorf and Augustin (Phosphorus and Sulfur 1981, 9, 329), a solution of 1.77 g (11.9 mmol) 3-(5-methyl-furan-2-yl)-3-oxo-propionitrile in 10 ml dry DMSO was added dropwise to a stirred suspension of 0.95 g (23.7 mmol, 60% dispersion in mineral oil) sodium hydride in 10 ml DMSO under argon at room temperature. 0.72 ml (11.9 mmol) carbon disulfide was then added dropwise, with external water bath cooling, and stirring continued for 1 hour, after which 1.48 ml (23.7 mmol) methyl iodide was added dropwise, with external water bath cooling, and stirring continued for a further 1 h. The reaction mixture was then poured into 300 ml ice-cold water, and the precipitate collected by filtration and dried in vacuo to afford 2.67 g (89%) 2-(5-methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile as a yellow crystalline solid. ES-MS m/e (%): 254 (M+H+, 100).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. waitcontinued for a further 1 h
  5. filtrationthe precipitate collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-211586d5256e48c9aa8e5ecfbc6f03cb
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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