Sulfuric Acid → HCID 70357358, compound

HRID 1651648Notes

Reaction equation

HRID 1651648 reaction equation
COCCO[CH2:6][O:7][CH:8]([C:10]1[CH:11]=[C:12]([S:16]([NH2:19])(=[S:18])=[O:17])[S:13][C:14]=1[CH3:15])[CH3:9].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>CO>[CH3:6][O:7][CH:8]([C:10]1[CH:11]=[C:12]([S:16]([NH2:19])(=[S:18])=[O:17])[S:13][C:14]=1[CH3:15])[CH3:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 131716394HCID 131716394, compound

Product 1

HCID 70357358HCID 70357358, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-[1-(methoxyethoxymethoxy)ethyl]-5-methylthiothiophene-2-sulfonamide (6.8 g, 0.02 mol) in methanol (25 ml) was added dropwise 50% (by volume) cold sulfuric acid (50 ml) over a 10 minute period. The solution was stirred for an additional 1/2 hour at room temperature and the mixture was basified with NaHCO3 with cooling. The gum which separated was extracted into ethyl acetate. The aqueous layer was concentrated to dryness in vacuo and the solid residue was extracted with hot ethyl acetate. The ethyl acetate extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give an amber liquid which was purified by chromatography on silica gel (100 g) using ethyl acetate (40%)/hexane (60%). There was recovered 1.9 g (36%) of white solid, m.p. 86-94° C.

Workup

  1. temperaturewith cooling
  2. customThe gum which separated
  3. extractionwas extracted into ethyl acetate
  4. concentrationThe aqueous layer was concentrated to dryness in vacuo
  5. extractionthe solid residue was extracted with hot ethyl acetate
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an amber liquid which
  10. customwas purified by chromatography on silica gel (100 g)
  11. customThere was recovered 1.9 g (36%) of white solid, m.p. 86-94° C.

Sources & evidence

ORD record
ord-9675b642dec64eb9b7ba97fb939aa224
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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