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

HRID 369606Notes

Reaction equation

HRID 369606 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-f145a09cadff4fcca304697a17b55005
Source dataset
uspto-grants-2000_10
Patent number
US06140270

Reaction notes

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