Hydrochloric Acid → 2-Sulfamoylthieno[2,3-c]pyridin-7(6H)-one

HRID 569055Notes

Reaction equation

HRID 569055 reaction equation
CN(C)C=[N:4][S:5]([C:8]1[S:20][C:11]2=[C:12]([O:16]C(=O)C)[N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1)(=[O:7])=[O:6].Cl>[OH-].[Na+].O>[S:5]([C:8]1[S:20][C:11]2[C:12](=[O:16])[NH:13][CH:14]=[CH:15][C:10]=2[CH:9]=1)(=[O:6])(=[O:7])[NH2:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53999326N,N-Dimethyl-N'-(7-acetoxythieno[2,3-c]pyridine-2-sulfonyl)formamidine

Product 1

HCID 201485872-Sulfamoylthieno[2,3-c]pyridin-7(6H)-oneYield 54.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

An initial suspension of N,N-dimethyl-N'-(7-acetoxythieno[2,3-c]pyridine-2-sulfonyl)formamidine (2.0 g, 6.1 mmol) in 10 N sodium hydroxide (4 ml) diluted with water (15 ml) was warmed at 60° C. for 1 hour. This clear solution was cooled and acidified with concentrated hydrochloric acid to give a precipitate of product. This precipitate (1.2 g) was collected by filtration and dried in a vacuum oven. Recrystallization by dissolution in a minimum amount of hot dimethyl sulfoxide, followed by dilution with ethanol gave 0.76 g (54% yield) of pure product; m.p. 295°-297° C.

Workup

  1. temperatureThis clear solution was cooled
  2. customto give a precipitate of product
  3. filtrationThis precipitate (1.2 g) was collected by filtration
  4. customdried in a vacuum oven
  5. customRecrystallization
  6. dissolutionby dissolution in a minimum amount of hot dimethyl sulfoxide

Sources & evidence

ORD record
ord-6c9c05014a6a42bfb097905c2ada8594
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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