Sulfuric Acid → HCID 14700389, compound

HRID 1651646Notes

Reaction equation

HRID 1651646 reaction equation
COCCOC[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([S:19]([NH2:22])(=[O:21])=[O:20])[S:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16].S(=O)(=O)(O)O>CO>[OH:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([S:19]([NH2:22])(=[O:20])=[O:21])[S:13][C:14]=1[S:15]([CH3:18])(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 53964772HCID 53964772, compound

Product 1

HCID 14700389HCID 14700389, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The 4-[2-(methoxyethoxymethoxy)ethyl]-5-methylsulfonylthiophene-2-sulfonamide (6.6 g, 0.0177 mol) was dissolved in methanol (25 ml) and was stirred at room temperature as cold 50% (v/v) sulfuric acid (40 ml) was added dropwise over 10 minutes. An additional quantity of methanol (25 ml) was added to dissolve the gum which separated and the solution was stirred for 1/2 hour. The solution was basified with sodium hydroxide and was washed with ether. The solution was acidified with HCl and was extracted with CHCl3 and then with ethyl acetate. The ethyl acetate extract was washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature to give 4.1 g of crude oil which was chromatographed on silica gel (100 g) eluting with 5% methanol in chloroform. There was recovered 2.5 g of white solid which provided 1.5 g of analytically pure, material, m.p. 120-124° C.

Workup

  1. additionwas added dropwise over 10 minutes
  2. dissolutionto dissolve the gum which
  3. customseparated
  4. washwas washed with ether
  5. extractionwas extracted with CHCl3
  6. extractionThe ethyl acetate extract
  7. washwas washed with saturated NaCl solution
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-813d90fba72449de8e155e364baa9432
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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