Ammonium Hydroxide → 4-Benzoyl-3-n-butoxy-5-sulfamylbenzoic acid

HRID 328964Notes

Reaction equation

HRID 328964 reaction equation
[C:1]([C:9]1[C:17]([S:18](Cl)(=[O:20])=[O:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:28]>>[C:1]([C:9]1[C:17]([S:18](=[O:20])(=[O:19])[NH2:28])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 214401184-Benzoyl-3-n-butoxy-5-chlorosulfonylbenzoic acid

Product 1

HCID 537122234-Benzoyl-3-n-butoxy-5-sulfamylbenzoic acid

Procedure

4-Benzoyl-3-n-butoxy-5-chlorosulfonylbenzoic acid (1.5 g) is in portions added to conc. ammonium hydroxide (15 ml) while stirring at 10°-12° C. After additional stirring at room temperature for 16 hours, the mixture is left in a refrigerator for 4-5 hours. The separated ammonium salt is collected by filtration and washed with a small amount of icecold water. After drying, the salt is dissolved in 1 N sodium hydroxide (15 ml) and the solution is dropwise added to icecold 1 N acetic acid (20 ml) while stirring. The separated material is collected by filtration, washed with water and dried in the air. The product is recrystallized from aqueous ethanol, and the thus purified material is dissolved in 1 N NaOH (15 ml). The solution is dropwise added to icecold 1 N acetic acid (18 ml) while stirring. The precipitated material is collected by filtration, washed with water and dried in vacuo in the presence of P2O5, to give 4-benzoyl-3-n-butoxy-5-sulfamylbenzoic acid.

Workup

  1. stirringAfter additional stirring at room temperature for 16 hours
  2. filtrationThe separated ammonium salt is collected by filtration
  3. washwashed with a small amount of icecold water
  4. customAfter drying
  5. dissolutionthe salt is dissolved in 1 N sodium hydroxide (15 ml)
  6. additionthe solution is dropwise added to icecold 1 N acetic acid (20 ml)
  7. stirringwhile stirring
  8. filtrationThe separated material is collected by filtration
  9. washwashed with water
  10. customdried in the air
  11. customThe product is recrystallized from aqueous ethanol
  12. dissolutionthe thus purified material is dissolved in 1 N NaOH (15 ml)
  13. additionThe solution is dropwise added to icecold 1 N acetic acid (18 ml)
  14. stirringwhile stirring
  15. filtrationThe precipitated material is collected by filtration
  16. washwashed with water
  17. dry with materialdried in vacuo in the presence of P2O5

Sources & evidence

ORD record
ord-69268f2b46d545a5aeb16e6562826d7f
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

Loading…