Dimethyl Sulfoxide → HCID 86583759, compound

HRID 1356171Notes

Reaction equation

HRID 1356171 reaction equation
[P].[S].[CH3:3][O:4][CH2:5][C:6]1[O:10][C:9]([C:11](=[O:15])[CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.[H-].[Na+].[C:18](=S)=[S:19].CI.[CH3:23][S:24]([CH3:26])=O>>[CH3:3][O:4][CH2:5][C:6]1[O:10][C:9]([C:11]([C:12](=[C:23]([S:19][CH3:18])[S:24][CH3:26])[C:13]#[N:14])=[O:15])=[CH:8][CH:7]=1

Participants

8

Reactant 7

HCID 679Dimethyl Sulfoxide2×HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 5362487SulfurHCID 5462309PhosphorusHCID 18507443HCID 18507443, compound

Product 1

HCID 86583759HCID 86583759, compoundYield 71%

Procedure

Following the method of Rudorf and Augustin (Phosphorus and Sulfur 1981, 9, 329), a solution of 1.00 g (5.58 mmol) 3-(5-methoxymethyl-furan-2-yl)-3-oxo-propionitrile in 15 ml dry DMSO was added dropwise to a stirred suspension of 487 mg (11.2 mmol, 60% dispersion in mineral oil) sodium hydride in 15 ml DMSO under argon at room temperature. 0.34 ml (5.58 mmol) carbon disulfide was then added dropwise, with external water bath cooling, and stirring continued for 2 hour, after which 0.70 ml (11.2 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 200 ml ice-cold water, and the precipitate collected by filtration, washed with hexane, and dried in vacuo to afford 1.12 g (71%) 2-(5-methoxymethyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile as a brown crystalline solid. EI-MS m/e (%): 283 (M+, 7), 282 ([M—H]+, 6), 268 ([M—CH3]+, 50), 266 ([M—OH]+, 35), 252 ([M—OCH3]+, 21), 238 ([M—CH2OCH3]+, 100), 139 (61).

Workup

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

Sources & evidence

ORD record
ord-186f3f1eb5aa43c081a81575b4b08ea8
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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