Ammonium Hydroxide → HCID 21546845, compound

HRID 1605549Notes

Reaction equation

HRID 1605549 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:24](Cl)(=[O:26])=[O:25])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:29]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:24](=[O:26])(=[O:25])[NH2:29])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 21546882HCID 21546882, compound

Product 1

HCID 21546845HCID 21546845, compound

Procedure

3-Benzyloxy-5-chlorosulfonyl-4-phenylbenzoic acid (1.0 g) is in portions added to conc. ammonium hydroxide (10 ml), while stirring at 10°-12° C. After additional stirring at room temperature for 18-20 hours, the mixture is left in a refrigerator for 2-3 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 (10 ml) and the 3-benzyloxy-4-phenyl-5-sulfamylbenzoic acid is precipitated by the dropwise addition of the solution to 1 N hydrochloric acid (12 ml). The acid is collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, it is obtained with a melting point of 199°-200° C.

Workup

  1. stirringAfter additional stirring at room temperature for 18-20 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 (10 ml)
  6. customthe 3-benzyloxy-4-phenyl-5-sulfamylbenzoic acid is precipitated by the dropwise addition of the solution to 1 N hydrochloric acid (12 ml)
  7. filtrationThe acid is collected by filtration
  8. washwashed with water
  9. customdried
  10. customAfter recrystallization from aqueous ethanol
  11. customit is obtained with a melting point of 199°-200° C.

Sources & evidence

ORD record
ord-60d4748dffa74d9b95887cf59070f95b
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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