Hydrochloric Acid → HCID 21520084, compound

HRID 1282771Notes

Reaction equation

HRID 1282771 reaction equation
[Cl:1][C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[SH:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O.[OH-].[Na+]>[CH2:16]([S:15][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[Cl:1])[C:6]([OH:8])=[O:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 21520058HCID 21520058, compound

Product 1

HCID 21520084HCID 21520084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Chloro-3-mercapto-5-sulfamylbenzoic acid (0.27 g) is dissolved in water (25 ml) by addition of 1 N sodium hydroxide until pH 8. Benzyl bromide (0.15) is added and the reaction mixture stirred for 18 hours. Addition of 4 N hydrochloric acid until pH 1.5 precipitates a crude material which is collected by filtration, washed with water, and recrystallized from aqueous ethanol to yield 3-benzylthio-4-chloro-5-sulfamylbenzoic acid with a melting point of 241° - 242.5°C.

Workup

  1. customprecipitates a crude material which
  2. filtrationis collected by filtration
  3. washwashed with water
  4. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-a70f63cdff23447fbade9923fb2e84e3
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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