1,2-Benzisothiazol-3(2H)-one → HCID 53863787, 화합물

HRID 1284537노트

반응식

HRID 1284537 반응식
[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]

참가 물질

5

반응물 3

HCID 175201,2-Benzisothiazol-3(2H)-oneHCID 24758Sodium hydrideHCID 20252124HCID 20252124, 화합물

생성물 1

HCID 53863787HCID 53863787, 화합물수율 23%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-54812968b0764935b23493d2f8ac2029
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04563474

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