Water → Isamoxole

HRID 613996ノート

反応式

HRID 613996 の反応式
C([C:5]([CH3:10])([CH3:9])[C:6]([NH2:8])=[O:7])CCC.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[CH3:16][C:17]1[N:18]=[C:19](S(C)=O)[O:20][CH:21]=1.O>C1COCC1>[CH2:11]([N:8]([C:19]1[O:20][CH:21]=[C:17]([CH3:16])[N:18]=1)[C:6](=[O:7])[CH:5]([CH3:9])[CH3:10])[CH2:12][CH2:13][CH3:14]

参加物

6

反応物 4

HCID 962WaterHCID 181100Hexanamide, 2,2-dimethyl-HCID 541594704-Methyl-2-methylsulphinyloxazoleHCID 178418339Butyllithium

生成物 1

HCID 42118Isamoxole収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

n-Butyl-isobutyramide (0.99 g, 0.0069 m) in dry THF (10 ml) was cooled to -20° C. under nitrogen during the dropwise addition of a 1.445 M solution of n-butyl lithium (4.8 ml, 0.0069 m). The mixture was stirred for 20 minutes at -20° C. and then 4-methyl-2-methylsulphinyloxazole (1.0 g, 0.0068 m) in dry THF (10 ml) was added rapidly and the mixture allowed to warm to 0° C. It was stirred at this temperature for 11/2 hours then allowed to warm to room temperature and stirred for a further 1/2 hour. The mixture was hydrolysed with water and the solvent was evaporated under reduced pressure. The residue was extracted with diethyl ether and the extract was evaporated. The resulting oil was chromatographed on silica using ether/hexane. The compound was distilled in vacuo to give the title compound as a colourless oil 1.21 g, (78%), b.p. (airbath) 70° C. at 0.01 mm.

後処理

  1. temperatureto warm to 0° C
  2. stirringIt was stirred at this temperature for 11/2 hours
  3. temperatureto warm to room temperature
  4. stirringstirred for a further 1/2 hour
  5. customthe solvent was evaporated under reduced pressure
  6. extractionThe residue was extracted with diethyl ether
  7. customthe extract was evaporated
  8. customThe resulting oil was chromatographed on silica
  9. distillationThe compound was distilled in vacuo

出典と根拠

ORDレコード
ord-54f32ab7f6744aa99fcfa55533e31fbd
出典データセット
uspto-grants-1979_03
特許番号
US04143047

反応ノート

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