Sulfuric Acid → HCID 14700386, compound

HRID 1651642Notes

Reaction equation

HRID 1651642 reaction equation
COCCOC[O:7][CH:8]([C:11]1[CH:12]=[C:13]([S:20]([NH2:23])(=[O:22])=[O:21])[S:14][C:15]=1[S:16]([CH3:19])(=[O:18])=[O:17])[CH2:9][CH3:10].S(=O)(=O)(O)O.[OH-].[Na+].CO.C(Cl)(Cl)Cl>CO.O>[OH:7][CH:8]([C:11]1[CH:12]=[C:13]([S:20]([NH2:23])(=[O:22])=[O:21])[S:14][C:15]=1[S:16]([CH3:19])(=[O:17])=[O:18])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14700385HCID 14700385, compoundHCID 21584188Chloroform methanol

Product 1

HCID 14700386HCID 14700386, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-[1-(methoxyethoxymethoxy)propyl]-5-methylsulfonylthiophene-2-sulfonamide (8.0 g, 0.02 mol) in methanol (20 ml) was added a cold solution of concentrated sulfuric acid (20 ml) in water (20 ml). The mixture was stirred at room temperature for 1 hour and the solution was basified with a slight excess of 40% NaOH and the suspension was filtered to remove precipitated salts. The filtrate was washed with ether and acidified with HCl. The acidified mixture was extracted with ethyl acetate (4×25 ml). The combined extracts were washed with saturated NaCl solution and dried over anhydrous Na2SO4. The solution was filtered and concentrated in vacuo at room temperature to give a viscous yellow oil which was a mixture of five components. Chromatography on 300 g of silica gel eluting with 5% methanol/CHCl3 gave 3.0 g of a pure colorless oil. Trituration of the oil in n-butyl chloride gave a white solid (2.8 g) (45%). The product was recrystallized from 1,2-dichloroethane; m.p. 125.5-126.5° C.

Workup

  1. filtrationthe suspension was filtered
  2. customto remove
  3. customprecipitated salts
  4. washThe filtrate was washed with ether
  5. extractionThe acidified mixture was extracted with ethyl acetate (4×25 ml)
  6. washThe combined extracts were washed with saturated NaCl solution
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo at room temperature
  10. customto give a viscous yellow oil which
  11. additiona mixture of five components

Sources & evidence

ORD record
ord-276fa6e9d6974e1aaa4b4aaa906ea0d3
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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