Benzyl Bromide → HCID 21520060, compound

HRID 1282791Notes

Reaction equation

HRID 1282791 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([S:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 21520079HCID 21520079, compound

Product 1

HCID 21520060HCID 21520060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Mercapto-4-phenoxy-5-sulfamylbenzoic acid (0.6 g) is suspended in water (20 ml) and the pH is adjusted to 8 by addition of 1 N sodium hydroxide. Benzyl bromide (0.35 g) is added to the resulting solution, and the reaction mixture is stirred for 2 hours at room temperature. After cooling, the precipitated sodium salt of 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration. The salt is dissolved in hot water (60 ml) and the solution acidified by addition of 1 N hydrochloric acid. After cooling, the precipitated 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration and recrystallized from aqueous ethanol to yield the desired compound with a melting point of 234°-236°C., after drying in vacuo.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated sodium salt of 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration
  3. dissolutionThe salt is dissolved in hot water (60 ml)
  4. additionthe solution acidified by addition of 1 N hydrochloric acid
  5. temperatureAfter cooling
  6. filtrationthe precipitated 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-3bd6afdb58f1402d8ddbd254ab2485cf
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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