Hydrochloric Acid → [(5-Nitro-1,2-benzisothiazol-3-yl)oxy]acetonitrile

HRID 1274601노트

반응식

HRID 1274601 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][NH:10][C:9](=[O:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]#[N:23].Cl>CN(C)C=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([O:12][CH2:21][C:22]#[N:23])[C:8]=2[CH:13]=1)([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 131869501,2-Benzisothiazol-3(2H)-one, 5-nitro-

생성물 1

HCID 18314467[(5-Nitro-1,2-benzisothiazol-3-yl)oxy]acetonitrile수율 71.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 5-nitro-1,2-benzisothiazol-3(2H)-one (17.5 g, 89.2 mmol) in N,N-dimethylformamide is treated with potassium carbonate (18.5 g, 134 mmol), stirred at room temperature for 30 minutes, treated with bromoacetonitrile (16.0 g, 133 mmol), stirred at room temperature overnight, and poured onto ice. The resultant aqueous mixture is acidified to pH 3 with hydrochloric acid and extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Column chromatography of the solid using silica gel and methylene chloride gives the title product as a yellow solid (15.0 g, mp 123-124.5° C.).

후처리

  1. stirringstirred at room temperature overnight
  2. additionpoured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a solid

출처 및 근거

ORD 기록
ord-e8a5ac6d85604fa8bad03b331a14b8f3
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156700

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