Methanol → Methyl 2-[(3-hydroxypropyl)sulfonyl]-5-sulfamoylbenzoate

HRID 2118580Notes

Reaction equation

HRID 2118580 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:7]=1[C:16]([OH:18])=[O:17].OS(O)(=O)=O.[CH3:24]O>>[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:7]=1[C:16]([O:18][CH3:24])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13960351HCID 13960351, compound

Product 1

HCID 13960352Methyl 2-[(3-hydroxypropyl)sulfonyl]-5-sulfamoylbenzoate

Procedure

4-(3-hydroxypropylthio)-3-carboxybenzene-sulfonamide (15 g, 0.0515 mol) and concentrated H2SO4 (4 ml) were dissolved in methanol (150 ml) and refluxed on a steam bath for about 5 hours. The solvent was removed and the residue was treated with water. The mixture was extracted with ethylacetate, which was washed with water, saturated sodium bicarbonate, water and brine. After drying, removal of the solvent left a tannish solid. Recrystallization from 1,2-dichloroethane gave 13.5 g of a white solid. M.p.=123°-125°.

Workup

  1. temperaturerefluxed on a steam bath for about 5 hours
  2. customThe solvent was removed
  3. additionthe residue was treated with water
  4. extractionThe mixture was extracted with ethylacetate, which
  5. washwas washed with water, saturated sodium bicarbonate, water and brine
  6. customAfter drying
  7. customremoval of the solvent
  8. waitleft a tannish solid
  9. customRecrystallization from 1,2-dichloroethane

Sources & evidence

ORD record
ord-6f0fe8d684c841c9b62bd4e57bf96653
Source dataset
uspto-grants-1987_07
Patent number
US04678855

Reaction notes

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