Ethylene Oxide → 2-Sulfamoyl-6-(2-hydroxyethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 569051Notes

Reaction equation

HRID 569051 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].[CH2:14]1[O:16][CH2:15]1>CO.C(#N)C>[S:1]([C:5]1[S:13][C:8]2[CH2:9][N:10]([CH2:14][CH2:15][OH:16])[CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

5

Reactant 2

HCID 6354Ethylene OxideHCID 201485892-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 201485792-Sulfamoyl-6-(2-hydroxyethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Into a solution of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (1.74 g, 8.0 mmol) in methanol (25 ml) and acetonitrile (50 ml) was bubbled ethylene oxide gas for 10 minutes. The reaction vessel was stoppered and the mixture was stirred for 18 hours. The precipitated product was collected by filtration. The filtrates were concentrated to provide additional product (total weight, 2.02 g). This material was crystallized from acetonitrile to give 1.67 g (80% yield) of pure product; m.p. 184°-186° C.

Workup

  1. filtrationThe precipitated product was collected by filtration
  2. concentrationThe filtrates were concentrated
  3. customto provide additional product (total weight, 2.02 g)
  4. customThis material was crystallized from acetonitrile

Sources & evidence

ORD record
ord-66ed44e2459c46779b3a0b1a8964cfca
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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