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

HRID 569047
Notes
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Reaction equation

HRID 569047 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 201485892-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 20148577Thieno[2,3-c]pyridine-2-sulfonamideYield 34.9%

Reagents, catalysts & solvents 2

HCID 178511488
HCID 178511488, compound
Catalyst
HCID 962WaterSolvent3×

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

  1. extractionThe product was extracted from this solution with ethyl acetate
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered through a pad of charcoal
  4. customevaporated
  5. customto give 5.5 g of crude product
  6. customThis material was chromatographed on silica gel
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes