Water → HCID 14700402, compound

HRID 1651656Notes

Reaction equation

HRID 1651656 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][C:3]=1[CH:11]([O:13]COCCOC)[CH3:12].O>CO>[Br:1][C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:8])=[O:9])=[CH:4][C:3]=1[CH:11]([OH:13])[CH3:12]

Participants

4

Reactant 2

HCID 962WaterHCID 54086540HCID 54086540, compound

Product 1

HCID 14700402HCID 14700402, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-4-[l-(methoxyethoxymethoxy)ethyl]thiophene-2-sulfonamide (5.3 g, 0.014 mol) was dissolved in methanol (25 ml) and water (25 ml) was added. Some oil separated. To this stirred mixture was added sulfuric acid (25 ml) dropwise with cooling over 20 minutes. The resulting solution was stirred at room temperature over night. The methanol was removed in vacuo and the residual suspension was diluted with two volumes of water. The product was extracted into ethyl acetate. The extract was washed with saturated NaHCO3, water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. This gave 4.0 g of a viscous amber oil. The crude oil was chromatographed on silica gel (150 ml) eluting with 5% methanol/chloroform to give 1.96 g of colorless oil which showed a single spot by TLC. Trituration of the oil in n-butyl chloride gave a white solid (1.69 g, 49%), m.p. 126-128.5° C. NMR supported the structure.

Workup

  1. customSome oil separated
  2. additionTo this stirred mixture was added sulfuric acid (25 ml) dropwise
  3. temperaturewith cooling over 20 minutes
  4. customThe methanol was removed in vacuo
  5. additionthe residual suspension was diluted with two volumes of water
  6. extractionThe product was extracted into ethyl acetate
  7. washThe extract was washed with saturated NaHCO3, water
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude oil was chromatographed on silica gel (150 ml)
  12. washeluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-835c2dc7aee24ef5b2cad1135d573465
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

Loading…