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

HRID 1274602Notes

Reaction equation

HRID 1274602 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[C:13]([O:16][CH2:17][C:18]#[N:19])[C:12]=2[CH:20]=1)([O-])=O>[Fe].C(OCC)(=O)C>[NH2:5][C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[C:13]([O:16][CH2:17][C:18]#[N:19])[C:12]=2[CH:20]=1

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 18314467[(5-Nitro-1,2-benzisothiazol-3-yl)oxy]acetonitrile

Product 1

HCID 18314508[(5-Amino-1,2-benzisothiazol-3-yl)oxy]acetonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of iron powder (13.0 g, 0.233 mol) in a 5% acetic acid solution (65.0 mL) is heated to 50° C., treated portionwise with a mixture of [(5-nitro-1,2-benzisothiazol-3-yl)oxy]acetonitrile (11.0 g, 0.047 mol), acetic acid (100 mL) and ethyl acetate (65.0 mL), refluxed for two hours, cooled to 40° C., and filtered to remove solids. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phase and the organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as an oil which is identified by NMR spectral analysis.

Workup

  1. temperaturerefluxed for two hours
  2. temperaturecooled to 40° C.
  3. filtrationfiltered
  4. customto remove solids
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. washwashed sequentially with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-574c83ab198742829832e4fd193dd92f
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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