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

HRID 569049Notes

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(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[S:1]([C:5]1[S:13][C:8]2[CH:9]=[N:10][CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a partial suspension of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (3.05 g, 14 mmol) in ethyl acetate (200 ml) was added activated manganese dioxide (3.0 g). This mixture was warmed to 80° C. Every two hours an additional 3.0 g of activated manganese dioxide was added until 12 g total had been added. This mixture was filtered hot and the collected manganese dioxide was re-extracted with hot ethyl acetate. The combined ethyl acetate extracts were evaporated to give 2.1 g of crude product. This material was purified by chromatography on silica gel eluting with a gradient 0-5% methanol/ethyl acetate. Recrystallization from ethyl acetate gave pure product (0.8 g, 26.5% yield); m.p. 161°-164° C.

Workup

additionhad been added
filtrationThis mixture was filtered hot
extractionthe collected manganese dioxide was re-extracted with hot ethyl acetate
customThe combined ethyl acetate extracts were evaporated
customto give 2.1 g of crude product
customThis material was purified by chromatography on silica gel eluting with a gradient 0-5% methanol/ethyl acetate
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-6c2faa2194c74971a021659bf646e7f7
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04731368

Reaction notes

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