Acetic Acid → 1,2-Benzisothiazol-5-amine

HRID 252148Notes

Reaction equation

HRID 252148 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.CC(O)=O>O.CCOC(C)=O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[CH:9][C:8]=2[CH:12]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 1984101,2-Benzisothiazole, 5-nitro-

Product 1

HCID 1982931,2-Benzisothiazol-5-amineYield 86.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

5-Nitrobenzo[d]isothiazole (305 mg, 1.69 mmol), 5% AcOH (aq.) (12 mL) and EtOAc (12 mL) at 65° C. was treated with iron powder (325 mesh, 473 mg) and stirred rapidly for 1 h. The mixture was cooled to ambient temperature, diluted with water and EtOAc and filtered through dicalite. The organic layer was separated and the aqueous layer extracted with further EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (220 mg, 85%).

Workup

  1. filtrationfiltered through dicalite
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with further EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6da29744de624849af940fc5ceb9fdeb
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Reaction notes

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