Butyl iodide → 5-Amino-3-n-butylthio-4-phenoxybenzoic acid

HRID 1282779Notes

Reaction equation

HRID 1282779 reaction equation
[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([SH:11])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[OH-].[Na+].[CH2:21](I)[CH2:22][CH2:23][CH3:24]>O>[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:4]([S:11][CH2:21][CH2:22][CH2:23][CH3:24])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 215201075-Amino-3-mercapto-4-phenoxybenzoic acid

Product 1

HCID 536718655-Amino-3-n-butylthio-4-phenoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Amino-3-mercapto-4-phenoxybenzoic acid (5.22 g) is suspended in water (150 ml), 1 N sodium hydroxide is added until pH 8, and n-butyl iodide (7.4 g) is added to the resulting solution. The reaction mixture is stirred for 16 hours whereafter 5-amino-3-n-butylthio-4-phenxoybenzoic acid is precipitated by addition of 1 N hydrochloric acid until pH 2.5. After collection, recrystallization from aqueous ethanol, and drying in vacuo at 65°C, the compound is obtained with a melting point of 131°-132°C.

Workup

  1. additionis added to the resulting solution
  2. customis precipitated by addition of 1 N hydrochloric acid until pH 2.5
  3. customAfter collection, recrystallization from aqueous ethanol
  4. customdrying in vacuo at 65°C
  5. customthe compound is obtained with a melting point of 131°-132°C.

Sources & evidence

ORD record
ord-c788b412f54e4738b2dd944828f063b2
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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