Acetic Acid → 5-Amino-6-fluoro-3-methyl-1,2-benzisothiazole

HRID 1274573Notes

Reaction equation

HRID 1274573 reaction equation
[F:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][S:8][C:4]=2[CH:3]=1.C(O)(=O)C>[Fe].C(OCC)(=O)C>[NH2:12][C:11]1[C:2]([F:1])=[CH:3][C:4]2[S:8][N:7]=[C:6]([CH3:9])[C:5]=2[CH:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 183144696-Fluoro-3-methyl-5-nitro-1,2-benzisothiazole

Product 1

HCID 120568325-Amino-6-fluoro-3-methyl-1,2-benzisothiazoleYield 95.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 6-fluoro-3-methyl-5-nitro-1,2-benzisothiazole (0.740 g, 3.50 mmol), 5% acetic acid (25.0 mL) and ethyl acetate is heated to 65° C., treated with iron powder (0.980 g, 17.5 mmol), stirred at 65° C. for one hour, cooled to room temperature, and filtered to remove solids. The organic phase is separated, washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as an orange solid (0.610 g) which is identified by NMR spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customto remove solids
  4. customThe organic phase is separated
  5. washwashed sequentially with water, saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11b44e1c7f4e481b89b193839d0d5875
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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