Ammonium Hydroxide → HCID 21440164, compound

HRID 328965Notes

Reaction equation

HRID 328965 reaction equation
[CH2:1]([C:8]1[C:16]([S:17](Cl)(=[O:19])=[O:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:30]>>[CH2:1]([C:8]1[C:16]([S:17](=[O:19])(=[O:18])[NH2:30])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 21440237HCID 21440237, compound

Product 1

HCID 21440164HCID 21440164, compound

Procedure

4-Benzyl-3-benzyloxy-5-chlorosulfonylbenzoic 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 about 20 hours, the mixture is left in a refrigerator for 4-5 hours. The separated ammonium salt is then collected by filtration and washed with a small amount of ice-cold water. After drying, the salt is dissolved in hot water (20 ml), and the solution is clarified by filtration hot in the presence of decolorizing carbon. The solution is then acidified with 4 N HCl (2.0 ml) and, after cooling, the resulting precipitate is collected by filtration, washed with water and dried. After recrystallization twice from ethanol, 4-benzyl-3-benzyloxy-5-sulfamylbenzoic acid is obtained with a melting point of 249.5°-251° C.

Workup

  1. stirringAfter additional stirring at room temperature for about 20 hours
  2. filtrationThe separated ammonium salt is then collected by filtration
  3. washwashed with a small amount of ice-cold water
  4. customAfter drying
  5. dissolutionthe salt is dissolved in hot water (20 ml)
  6. filtrationthe solution is clarified by filtration hot in the presence of decolorizing carbon
  7. temperatureafter cooling
  8. filtrationthe resulting precipitate is collected by filtration
  9. washwashed with water
  10. customdried
  11. customAfter recrystallization twice from ethanol

Sources & evidence

ORD record
ord-8c456ed0cbb6451588be53fea0f01839
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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