Hydrochloric Acid → Thieno[2,3-c]pyridine-2-sulfonamide

HRID 569047Notes

Reaction equation

[OH-].[K+].[S:3]([C:7]1[S:15][C:10]2[CH2:11][NH:12][CH2:13][CH2:14][C:9]=2[CH:8]=1)(=[O:6])(=[O:5])[NH2:4].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[S:3]([C:7]1[S:15][C:10]2=[CH:11][N:12]=[CH:13][CH:14]=[C:9]2[CH:8]=1)(=[O:5])(=[O:6])[NH2:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of potassium ferricyanide (76 g, 0.23 mol) in water (400 ml) was added a solution of potassium hydroxide (68 g, 0.113 mol) in water (150 ml), followed by a suspension of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (10.8 g, 49.5 mmol) in water (50 ml). This mixture was warmed at 80° C. for 4-6 hours. This solution was acidified with concentrated hydrochloric acid and then made basic with saturated sodium carbonate solution. The product was extracted from this solution with ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated to give 5.5 g of crude product. This material was chromatographed on silica gel and eluted with ethyl acetate to give 3.7 g (34.9% yield) of pure product; m.p. 191°-193° C.

Workup

extractionThe product was extracted from this solution with ethyl acetate
dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
filtrationfiltered through a pad of charcoal
customevaporated
customto give 5.5 g of crude product
customThis material was chromatographed on silica gel
washeluted with ethyl acetate

Sources & evidence

ORD record: ord-b9fe50193e9a414bafc91b4dead63d8d
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04731368

Reaction notes

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