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

HRID 1355884Notes

Reaction equation

HRID 1355884 reaction equation
[P].[S].[CH3:3][C:4]1[CH:8]=[CH:7][O:6][C:5]=1[C:9](=[O:13])[CH2:10][C:11]#[N:12].[H-].[Na+].[C:16](=S)=[S:17].CI.[CH3:21][S:22]([CH3:24])=O>>[CH3:3][C:4]1[CH:8]=[CH:7][O:6][C:5]=1[C:9]([C:10](=[C:21]([S:17][CH3:16])[S:22][CH3:24])[C:11]#[N:12])=[O:13]

Participants

8

Reactant 7

HCID 679Dimethyl Sulfoxide2×HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 5362487SulfurHCID 5462309PhosphorusHCID 115283653-(3-Methylfuran-2-yl)-3-oxopropanenitrile

Product 1

HCID 865837502-(3-Methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrileYield 99%

Procedure

Following the method of Rudorf and Augustin (Phosphorus and Sulfur 1981, 9, 329), a solution of 4.4 g (29.5 mmol) 3-(3-methyl-furan-2-yl)-3-oxo-propionitrile in 30 ml dry DMSO was added dropwise to a stirred suspension of 2,4 g (59.0 mmol, 60% dispersion in mineral oil) sodium hydride in 20 ml DMSO under argon at room temperature. 1.8 ml (29.5 mmol) carbon disulfide was then added dropwise, with external water bath cooling, and stirring continued for 1 hour, after which 3.7 ml (59.0 mmol) methyl iodide was added dropwise, with external water bath cooling, and stirring continued for a further 16 h. The reaction mixture was then poured into 2 l ice-cold water, and the precipitate collected by filtration and dried in vacuo to afford 7.45 g (99%) 2-(3-methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile as a pale yellow crystalline solid. ES-MS m/e (%): 271 (M+NH4+, 33), 254 (M+H+, 100).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. waitcontinued for a further 16 h
  5. filtrationthe precipitate collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-dfcb681529c24b329f140dc094671919
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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