2-BENZOTHIAZOLESULFONAMIDE, 6-NITRO- → Aminozolamide

HRID 615356Notes

Reaction equation

HRID 615356 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 133934272-BENZOTHIAZOLESULFONAMIDE, 6-NITRO-

Product 1

HCID 93505AminozolamideYield 26.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Nitro-2-benzothiazolesulfonamide (2.93 g., 0.0113 mole) suspended in absolute ethanol (200 ml.) was hydrogenated in the presence of 5% palladium on carbon (2.9 g.) in a Parr apparatus. After 5 hrs. the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated to dryness to give the solid product. Recrystallization from ethyl acetate and reprecipitation by dissolution in dilute aqueous hydrochloric acid followed by treatment with aqueous sodium bicarbonate solution gave 680 mg 6-amino-2-benzothiazolesulfonamide, m.p. 227°-9° C. dec.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to dryness
  4. customto give the solid product
  5. customRecrystallization
  6. customfrom ethyl acetate and reprecipitation
  7. dissolutionby dissolution in dilute aqueous hydrochloric acid

Sources & evidence

ORD record
ord-c653603eed5a4b27a3d8e85a5be552b0
Source dataset
uspto-grants-1985_02
Patent number
US04499103

Reaction notes

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