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Hydrochloric Acid → 2-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 569048
Notes
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Reaction equation

HRID 569048 reaction equation
[S:1]([C:5]1[S:16][C:8]2[CH2:9][N:10](C(=O)C)[CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].Cl.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CO>[OH-].[Na+]>[S:1]([C:5]1[S:16][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 201485722-Sulfamoyl-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineHCID 21584119Ethylacetate methanol

Product 1

HCID 201485892-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 91.1%

Reagents, catalysts & solvents 1

HCID 14798
Sodium Hydroxide
Solvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-sulfamoyl-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (9.61 g, 37 mmol) in 20% sodium hydroxide solution (75 ml) was warmed at 80° C. for 3 hours. The resultant clear solution was cooled, acidified with concentrated hydrochloric acid, and then made basic with saturated sodium carbonate solution. The product was isolated by exhaustive extraction into ethyl acetate/methanol. The dried solution was evaporated to give 7.36 g (91% yield) of product. Recrystallization from ethyl acetate/methanol gave pure product; m.p. 172°-175° C.

Workup

  1. temperatureThe resultant clear solution was cooled
  2. customThe dried solution was evaporated

Sources & evidence

ORD record
ord-c67af48a0b7f4bc989bceca52911f178
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