Hydrochloric Acid → 4-(2-Sulfoethylamino)benzoic acid

HRID 904249Notes

Reaction equation

HRID 904249 reaction equation
[S:1]([CH2:5][CH2:6][NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1)([OH:4])(=[O:3])=[O:2].[OH-].[K+].C(O)C.Cl>O>[S:1]([CH2:5][CH2:6][NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)([OH:4])(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 21163340Ethyl 4-(2-sulfoethylamino)benzoate

Product 1

HCID 211633414-(2-Sulfoethylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4.4 g. of ethyl 4-(2-sulfoethylamino)benzoate, 2.3 g. of potassium hydroxide, 10 ml. of water, and 90 ml. of ethanol is stirred under reflux for 8 hours, allowed to cool, diluted with water, and brought to pH 4 with concentrated hydrochloric acid. The precipitate is collected by filtration, dried, and recrystallized from acetic acid to yield 4-(2-sulfoethylamino)benzoic acid as a white solid.

Workup

  1. additionA mixture of 4.4 g
  2. temperatureunder reflux for 8 hours
  3. temperatureto cool
  4. filtrationThe precipitate is collected by filtration
  5. customdried
  6. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-69bd1bfe07f9427dbd824fb10cbf926d
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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