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

HRID 636054ノート

反応式

HRID 636054 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-c7e02f69780540709793cbd62902ff74
出典データセット
uspto-grants-2001_02
特許番号
US06191275B1

反応ノート

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