Sodium hydride → (2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]thiazol-8-ylidene)acetonitrile

HRID 1039272ノート

反応式

HRID 1039272 の反応式
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][C:15]1[S:16][C:17]2[C:26]3[C:25](=O)[CH2:24][CH2:23][C:22]=3[CH:21]=[CH:20][C:18]=2[N:19]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:14][C:15]1[S:16][C:17]2[C:26]3[C:25](=[CH:3][C:1]#[N:2])[CH2:24][CH2:23][C:22]=3[CH:21]=[CH:20][C:18]=2[N:19]=1

参加物

6

反応物 4

HCID 24758Sodium hydride2 回HCID 75676Diethyl (cyanomethyl)phosphonate2 回HCID 516892Sodium BicarbonateHCID 577812782-Methyl-6,7-dihydro-8H-indeno[5,4-d]thiazol-8-one

生成物 1

HCID 67355527(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]thiazol-8-ylidene)acetonitrile収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of diethyl cyanomethylphosphonate (393 mg, 2.22 mmol) in tetrahydrofuran (6 mL) was added 65% sodium hydride (66.0 mg, 1.79 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Thereto was added a solution of 2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]thiazol-8-one (300 mg, 1.48 mmol) in tetrahydrofuran (6 mL), and the mixture was stirred at room temperature for 2 hr. To the mixture were added diethyl cyanomethylphosphonate (131 mg, 0.74 mmol) and 65% sodium hydride (16.0 mg, 0.43 mmol), and the mixture was further stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (181 mg, yield 54%).

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. stirringthe mixture was further stirred at room temperature for 30 min
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-a22f3cf40b0640cd8edb2d31045b904b
出典データセット
uspto-grants-2013_10
特許番号
US08552037B2

反応ノート

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