Acetic Acid → 1,2-Benzisothiazol-5-amine
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]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
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
- filtrationfiltered through dicalite
- customThe organic layer was separated
- extractionthe aqueous layer extracted with further EtOAc
- washThe combined organic extracts were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6da29744de624849af940fc5ceb9fdeb
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868017B2
Reaction notes
Loading…