2-BENZOTHIAZOLESULFONAMIDE, 6-NITRO- → Aminozolamide

HRID 1110372Notes

Reaction equation

HRID 1110372 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.[H][H]>[Pd].C(O)C>[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

5

Reactant 2

HCID 133934272-BENZOTHIAZOLESULFONAMIDE, 6-NITRO-HCID 178418361HCID 178418361, compound

Product 1

HCID 93505AminozolamideYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-nitrobenzothiazole-2-sulfonamide (3.0 g, 0.011 mol), 95% ethanol (290 ml), and 10% Pd on carbon (3.0 g) was hydrogenated at an initial pressure of 50 psig for 36 hours during which time the theoretical amount of hydrogen was consumed. The reduction mixture was vacuum filtered through a pad of Celite contained in a Buchner funnel and the volatiles removed under reduced pressure. The resulting product was purified by dissolving in aqueous 10% sodium carbonate (25 ml), filtering and adjusting the pH of the filtrate to 6 with glacial acetic acid. The precipitated product was collected by vacuum filtration in a Buchner funnel and dried under reduced pressure at 78° C. in an Abderhalden to give 2.2 g (82.9% yield) of 6-aminobenzothiazole-2-sulfonamide: m.p. 221°-222° C., Anal. (C7H7N3O2S2) CHN.

Workup

  1. customfor 36 hours
  2. customwas consumed
  3. filtrationfiltered through a pad of Celite
  4. customthe volatiles removed under reduced pressure
  5. customThe resulting product was purified
  6. dissolutionby dissolving in aqueous 10% sodium carbonate (25 ml)
  7. filtrationfiltering
  8. filtrationThe precipitated product was collected by vacuum filtration in a Buchner funnel
  9. customdried under reduced pressure at 78° C. in an Abderhalden

Sources & evidence

ORD record
ord-851236848eb3423382edd81225545814
Source dataset
uspto-grants-1990_12
Patent number
US04975448

Reaction notes

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