Hydrochloric Acid → 3-Amino-4-(3-hydroxypropane-1-sulfonyl)benzene-1-sulfonamide

HRID 2118579Notes

Reaction equation

HRID 2118579 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=1[N+:18]([O-])=O)(=[O:7])=[O:6].Cl>O.C(O)C.[Fe]>[OH:1][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:15])=[O:16])=[CH:10][C:9]=1[NH2:18])(=[O:6])=[O:7]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 139603654-(3-Hydroxypropane-1-sulfonyl)-3-nitrobenzene-1-sulfonamide

Product 1

HCID 139603693-Amino-4-(3-hydroxypropane-1-sulfonyl)benzene-1-sulfonamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(3-hydroxypropylsulfonyl)-3-nitrobenzenesulfonamide (4.0 g, 0.012 mol), iron powder (11 g), and 12M HCl (0.6 ml) in 10 ml water and 40 ml ethanol was refluxed on a steam bath for about 2 hours. The reaction mixture was filtered hot, and the solvent evaporated. The residue was taken up in ethyl acetate, washed with water, saturated sodium bicarbonate, water, then brine. After drying, evaporation of solvent left a residue that quickly crystallized. The solid was washed with water and collected. Recrystallization from butanol left 2.0 g of a white solid. M.p.=136.5°-138° C.

Workup

  1. temperaturewas refluxed on a steam bath for about 2 hours
  2. filtrationThe reaction mixture was filtered hot
  3. customthe solvent evaporated
  4. washwashed with water, saturated sodium bicarbonate, water
  5. customAfter drying
  6. customevaporation of solvent
  7. waitleft a residue that
  8. customquickly crystallized
  9. washThe solid was washed with water
  10. customcollected
  11. customRecrystallization from butanol
  12. waitleft 2.0 g of a white solid

Sources & evidence

ORD record
ord-f229a402beac43478fb0666d3892569d
Source dataset
uspto-grants-1987_07
Patent number
US04678855

Reaction notes

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