Acetic Acid → 2-Hydroxy-5-sulfamoylbenzoic acid

HRID 981062Notes

Reaction equation

HRID 981062 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].Br.C(O)(=O)C>C(OC(=O)C)C.CO>[NH2:13][S:12]([C:9]1[CH:10]=[CH:11][C:3]([OH:2])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6])(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 896012-Methoxy-5-sulfamoylbenzoic acid

Product 1

HCID 77312702-Hydroxy-5-sulfamoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 2-methoxy-5-sulfamoylbenzoic acid (58 g, 0.25 mole), 48% hydrobromic acid (150 ml), and acetic acid (150 ml) was heated to reflux for five hours. The progress of reaction was checked by thin layer chromatography (silica gel, 7:2:1 ethylacetate/methanol/29% ammonium hydroxide). Upon cooling, a solid crystallized out which was collected by filtration, and rinsed with cold water. This solid was dissolved in hot water (≤85° C.) and filtered through Celite® and recrystallized from the cool filtrate. Some of the recrystallized material was crystallized once more by dissolving in methanol, filtering, and mixing with excess amount of 1,1,1-trichloroethane. The mixture was evaporated to remove most of the methanol, and the resulting crystallizing mixture was stirred in ice bath. The solid was collected by filtration and rinsed with 1,1,1-trichloroethane, vacuum pumped at room temperature overnight to give a white solid, mp 234°-235° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for five hours
  3. customThe progress of reaction
  4. temperatureUpon cooling
  5. customa solid crystallized out which
  6. filtrationwas collected by filtration
  7. washrinsed with cold water
  8. dissolutionThis solid was dissolved in hot water (≤85° C.)
  9. filtrationfiltered through Celite®
  10. customrecrystallized from the cool filtrate
  11. customSome of the recrystallized material was crystallized once more
  12. dissolutionby dissolving in methanol
  13. filtrationfiltering
  14. additionmixing with excess amount of 1,1,1-trichloroethane
  15. customThe mixture was evaporated
  16. customto remove most of the methanol
  17. customthe resulting crystallizing mixture
  18. filtrationThe solid was collected by filtration
  19. washrinsed with 1,1,1-trichloroethane, vacuum
  20. customto give a white solid, mp 234°-235° C.

Sources & evidence

ORD record
ord-4592699936f64f34a2d1a8a5adf9fa76
Source dataset
uspto-grants-1991_02
Patent number
US04990523

Reaction notes

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