1,2-Benzisothiazol-3(2H)-one → HCID 53863787、化合物

HRID 1284537ノート

反応式

HRID 1284537 の反応式
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][NH:3]1.[H-].[Na+].Br[CH:14]([C:18]#[N:19])[C:15]([CH3:17])=[CH2:16]>CN(C)C=O>[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]1[CH2:16][C:15]([CH3:17])=[CH:14][C:18]#[N:19]

参加物

5

反応物 3

HCID 175201,2-Benzisothiazol-3(2H)-oneHCID 24758Sodium hydrideHCID 20252124HCID 20252124、化合物

生成物 1

HCID 53863787HCID 53863787、化合物収率 23%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

10.0 g (66 millimoles) of 2,3-dihydro-3-oxo-1,2-benzisothiazole were suspended in 140 ml of dimethylformamide, and 2.0 g (66 millimoles) of 80% strength sodium hydride were added a little at a time, while stirring thoroughly. After 15 minutes, 12.8 g (80 millimoles) of 3-bromo-2-methyl-3-cyanoprop-1-ene were slowly added dropwise, and the reaction mixture was stirred for 2 hours at 80° C. and then cooled. The solvent was distilled off under reduced pressure, the mixture was taken up in ice-water and extracted with methylene chloride, and the organic phase was washed thoroughly with H2O, dried and evaporated down. The crude product (16 g of a dark oil) was then purified by column chromatography (silica gel, mobile phase 95:5 mixture of methylene chloride and methanol). 3.5 g (23%) of 3-(2,3-dihydro-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylprop-1-ene of melting point 128°-130° C. were obtained.

後処理

  1. stirringthe reaction mixture was stirred for 2 hours at 80° C.
  2. temperaturecooled
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionextracted with methylene chloride
  5. washthe organic phase was washed thoroughly with H2O
  6. customdried
  7. customevaporated down
  8. customThe crude product (16 g of a dark oil) was then purified by column chromatography (silica gel, mobile phase 95:5 mixture of methylene chloride and methanol)

出典と根拠

ORDレコード
ord-54812968b0764935b23493d2f8ac2029
出典データセット
uspto-grants-1986_01
特許番号
US04563474

反応ノート

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