Hydrochloric Acid → (4-Aminophenylthio)acetic acid

HRID 1065990Notes

Reaction equation

HRID 1065990 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Cl[CH2:12][C:13]([O-:15])=[O:14].[Na+].Cl>CO.O>[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 23665759Sodium chloroacetate

Product 1

HCID 66907(4-Aminophenylthio)acetic acidYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a 500 ml three-necked flask were charged 60 ml of water, 120 ml of methanol and 75 g of sodium hydroxide. 75 g of 4-aminothiphenol and 85 g of sodium chloroacetate were then slowly added to the mixture over an ice bath. Thereafter, the reaction mixture was allowed to cool to room temperature where it was then stirred for 6 hours. After reaction, concentrated hydrochloric acid was added dropwise to the reaction mixture over an ice bath until the pH value of the solution reached 1. As a result, precipitation of a solid matter was observed. The precipitate was filtered off, thoroughly washed with water, and then dried to obtain 95 g of 4-aminophenylsulfanylacetic acid (white powder).

Workup

  1. additionwas added dropwise to the reaction mixture over an ice bath until the pH value of the solution
  2. customAs a result, precipitation of a solid matter
  3. filtrationThe precipitate was filtered off
  4. washthoroughly washed with water
  5. customdried

Sources & evidence

ORD record
ord-9b6a21f0f8f04fa7bfb11d29fb6d3817
Source dataset
uspto-grants-2001_06
Patent number
US06242155B1

Reaction notes

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