Allyl bromide → 3-Allylthio-5-amino-4-phenoxybenzoic acid

HRID 1282782Notes

Reaction equation

HRID 1282782 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].[CH2:19](Br)[CH:20]=[CH2:21]>C(=O)([O-])O.[Na+]>[CH2:21]([S:11][C:4]1[CH:5]=[C:6]([CH:10]=[C:2]([NH2:1])[C:3]=1[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]([OH:9])=[O:8])[CH:20]=[CH2:19]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 215201075-Amino-3-mercapto-4-phenoxybenzoic acid

Product 1

HCID 215200893-Allylthio-5-amino-4-phenoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 5-amino-3-mercapto-4-phenoxybenzoic acid (2.6 g) in saturated sodium hydrogen carbonate (120 ml) is cooled to 4°C. While cooling and stirring, allyl bromide (1 g) is added, and the reaction mixture is kept under nitrogen. After additional stirring for 10 minutes, 3-allylthio-5-amino-4-phenoxybenzoic acid is precipitated by addition of hydrochloric acid until pH 3. After collection by filtration, recrystallisation from aqeuous ethanol, and drying in vacuo, the compound is obtained with a melting point of 142°-143°C.

Workup

  1. temperatureWhile cooling
  2. stirringAfter additional stirring for 10 minutes
  3. custom3-allylthio-5-amino-4-phenoxybenzoic acid is precipitated by addition of hydrochloric acid until pH 3
  4. customAfter collection
  5. filtrationby filtration, recrystallisation from aqeuous ethanol
  6. customdrying in vacuo
  7. customthe compound is obtained with a melting point of 142°-143°C.

Sources & evidence

ORD record
ord-dc0af501f4224d15b1d1b4f99651e143
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

Loading…