Methanol → 2-Sulfamoyl-6-carbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 569050Notes

Reaction equation

HRID 569050 reaction equation
[S:1]([C:5]1[S:13][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].C[Si]([N:18]=[C:19]=[O:20])(C)C.CO>C(#N)C>[S:1]([C:5]1[S:13][C:8]2[CH2:9][N:10]([C:19](=[O:20])[NH2:18])[CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 70696Trimethylsilyl isocyanateHCID 201485892-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 201485902-Sulfamoyl-6-carbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a warm (40° C.) solution of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (1.42 g, 6.5 mmol) in acetonitrile (80 ml), under a nitrogen atmosphere, was added trimethylsilyl isocyanate (1.0 ml, 7.4 mmol). This solution was stirred for 19 hours and then methanol (2 ml) was added. After 2 hours the precipitated pure product was collected by filtration (1.62 g, 95% yield); m.p. 205°-208° C.

Workup

  1. filtrationAfter 2 hours the precipitated pure product was collected by filtration (1.62 g, 95% yield)

Sources & evidence

ORD record
ord-e4bea3d02dc24925b9d6c90d2ba756ea
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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