Chloroacetic Acid → (4-Aminophenylthio)acetic acid

HRID 1708847Notes

Reaction equation

HRID 1708847 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]([OH:15])=[O:14].C(=O)([O-])O.[Na+]>C(O)C.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 300Chloroacetic AcidHCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 66907(4-Aminophenylthio)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.6 parts of sodium hydroxide was dissolved in ethanol. A solution of 5 parts of p-aminothiophenol in 20 parts of ethanol was added to the solution. The mixture thus obtained was cooled at 0° C. or below. A solution of 3.8 parts of chloroacetic acid and 3.4 parts of sodium hydrogencarbonate in 10 parts of water was added dropwise to the mixture, while the mixture was kept at 0° C. or below. After completion of the addition, the mixture was stirred at 0° C. for 3 hours and then adjusted at pH 3. A solid thus formed was filtered to obtain 5.4 parts of p-aminothiophenoxyacetic acid.

Workup

  1. customThe mixture thus obtained
  2. temperaturewas cooled at 0° C. or below
  3. customwas kept at 0° C. or below
  4. additionAfter completion of the addition
  5. customA solid thus formed
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-bf7b1d7d42fb4dd8ae97b1d007923e24
Source dataset
uspto-grants-1990_08
Patent number
US04946761

Reaction notes

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