Acetic Acid → 7-Acetamino-4-acetoxy-1,2-benzisothiazole

HRID 1449117Notes

Reaction equation

HRID 1449117 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][N:10]=[CH:9][C:8]=2[C:7]([OH:13])=[CH:6][CH:5]=1)([O-])=O.[C:14]([OH:17])(=O)[CH3:15].[H][H].[C:20](OC(=O)C)(=[O:22])[CH3:21]>[Pd]>[NH:1]([C:4]1[C:12]2[S:11][N:10]=[CH:9][C:8]=2[C:7]([O:13][C:14](=[O:17])[CH3:15])=[CH:6][CH:5]=1)[C:20]([CH3:21])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 1357653737-Nitro-4-hydroxy-1,2-benzisothiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 203499417-Acetamino-4-acetoxy-1,2-benzisothiazoleYield 67%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

5.0 g of 7-nitro-4-hydroxy-1,2-benzisothiazole, in a mixture of 50 ml of acetic anhydride, 10 ml of acetic acid and 50 mg of a 5% strength palladium-on-charcoal catalyst, are left for 10 hours at 60° C. under 100 bars hydrogen pressure. After the mixture has cooled, the catalyst is filtered off, the filtrate is concentrated under reduced pressure and the partially crystalline crude product is recrystallized from acetic anhydride. 4.2 g (67% of theory) of 7-acetamino-4-acetoxy-1,2-benzisothiazole of melting point 215°-216° C. are obtained.

Workup

  1. temperatureAfter the mixture has cooled
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customthe partially crystalline crude product is recrystallized from acetic anhydride

Sources & evidence

ORD record
ord-16499a6ed4064bd39bd7dfdcf0158228
Source dataset
uspto-grants-1980_02
Patent number
US04189433

Reaction notes

Loading…