Dimethyl Sulfoxide → HCID 86583758、化合物

HRID 1356129ノート

反応式

HRID 1356129 の反応式
[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]=1

参加物

8

反応物 7

HCID 679Dimethyl Sulfoxide2 回HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 5362487SulfurHCID 5462309PhosphorusHCID 133193593-(5-Bromofuran-2-yl)-3-oxopropanenitrile

生成物 1

HCID 86583758HCID 86583758、化合物収率 65%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8cdf181173c040ee978ae717d06bea09
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

反応ノート

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