Dimethyl Sulfoxide → HCID 86583758, compound
Reaction equation
[P].[S].[Br: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>>[Br: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]=1Participants
Procedure
Following the method of Rudorf and Augustin (Phosphorus and Sulfur 1981, 9, 329), a solution of 3.02 g (14.1 mmol) 3-(5-bromo-furan-2-yl)-3-oxo-propionitrile in 25 ml dry DMSO was added dropwise to a stirred suspension of 1.13 g (28.3 mmol, 60% dispersion in mineral oil) sodium hydride in 25 ml DMSO under argon at room temperature. 0.85 ml (14.1 mmol) carbon disulfide was then added dropwise, with external water bath cooling, and stirring continued for 2 hour, after which 1.8 ml (28.3 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 1 l ice-cold water, and the precipitate collected by filtration, washed with hexane, and dried in vacuo to afford 2.91 g (65%) 2-(5-bromo-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile as a yellow crystalline solid. EI-MS m/e (%): 319 (M{81Br}+, 10), 317 (M{79Br}+, 10), 304 ([M{81Br}-CH3]+, 30), 302 ([M{79Br}-CH3]+, 45), 238 ([M—Br]+, 100), 223 (26), 210 (38), 195 (29), 175 (76), 173 (79), 95 (39), 38 (36).
Workup
- temperaturecooling
- temperaturecooling
- stirringstirring
- waitcontinued for a further 16 h
- filtrationthe precipitate collected by filtration
- washwashed with hexane
- customdried in vacuo
Sources & evidence
- ORD record
- ord-8cdf181173c040ee978ae717d06bea09
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586441B2
Reaction notes
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