HCID 21520058, compound → HCID 21520056, compound

HRID 1282769Notes

Reaction equation

HRID 1282769 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]>[OH-].[Na+].C(I)CCC>[CH2:10]([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])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 21520058HCID 21520058, compound

Product 1

HCID 21520056HCID 21520056, compound

Reagents, catalysts & solvents 2

HCID 10962Butyl iodideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 4-chloro-3-mercapto-5-sulfamylbenzoic acid (5.5 g) in 1 N sodium hydroxide (29.5 ml), butyl iodide (2.1 ml) is added. After additional stirring for 50 hours precipitates the sodium salt of 3-butylthio-4-chloro-5-sulfamylbenzoic acid which is collected and washed with ice water. The sodium salt is suspended in water (25 ml) and 1 N hydrochloric acid added slowly until a pH value of 1. The precipitate is collected by filtration and recrystallized from aqueous ethanol to yield 3-butylthio-4-chloro-5-sulfamylbenzoic acid with a melting point of 202° - 203°C.

Workup

  1. customprecipitates the sodium salt of 3-butylthio-4-chloro-5-sulfamylbenzoic acid which
  2. customis collected
  3. washwashed with ice water
  4. addition1 N hydrochloric acid added slowly until a pH value of 1
  5. filtrationThe precipitate is collected by filtration
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-424a794a44814793a384be8238cba619
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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