Sulfuric Acid → HCID 14700399, compound

HRID 1651653Notes

Reaction equation

HRID 1651653 reaction equation
COCCOC[O:7][CH:8]([C:10]1[S:14][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:12][C:11]=1[S:19]([CH3:22])(=[O:21])=[O:20])[CH3:9].S(=O)(=O)(O)O>CO.O>[OH:7][CH:8]([C:10]1[S:14][C:13]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:12][C:11]=1[S:19]([CH3:22])(=[O:20])=[O:21])[CH3:9]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14700398HCID 14700398, compound

Product 1

HCID 14700399HCID 14700399, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The 5-[1-(methoxyethoxymethoxy)ethyl]-4-methylsulfonylthiophene-2-sulfonamide (5.94 g, 0.0159 mol) was dissolved in 50/50 methanol/water (30 ml) with warming and concentrated sulfuric acid (15 ml) was added. The solution was cooled to ambient temperature and stirred for 1 hour. The methanol was removed in vacuo and the aqueous acid was diluted with water (50 ml). The product was extracted into ethyl acetate. The extract was washed with saturated NaHCO3 solution, water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. A colorless oil was obtained which solidified to a white solid. Several recrystallizations from water gave pure product (1.04 g, 23%), m.p. 121-127° C. NMR supported the structure and HPLC confirmed the purity.

Workup

  1. temperaturewith warming
  2. customThe methanol was removed in vacuo
  3. additionthe aqueous acid was diluted with water (50 ml)
  4. extractionThe product was extracted into ethyl acetate
  5. washThe extract was washed with saturated NaHCO3 solution, water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customA colorless oil was obtained which
  10. customSeveral recrystallizations from water

Sources & evidence

ORD record
ord-d81357ad550f4ef299ade29f819e1d3e
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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