Acetic Acid → Penicillamine

HRID 26578Notes

Reaction equation

HRID 26578 reaction equation
C(O)(=O)C.NC1C=CC=CC=1S.[CH3:13][C:14]1([CH3:36])[S:18]C(C(NC(CC2C=CC=CC=2)=O)C(O)=O)[NH:16][CH:15]1[C:33]([OH:35])=[O:34]>O>[NH2:16][C@@H:15]([C:33]([OH:35])=[O:34])[C:14]([SH:18])([CH3:36])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 87132-AminothiophenolHCID 98994Penicilloate

Product 1

HCID 5852Penicillamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.4 g (0.04 mole) of acetic acid in 20 ml of water, were added 1.38 g (0.011 mole) of o-aminothiophenol and 3.52 g (0.01 mole) of benzylpenicilloic acid. The mixture was heated under reflux, with stirring, for 2.5 hours in a nitrogen atmosphere. The reaction mixture was then treated as described in Example 6 to give D-penicillamine as colorless crystals: yield 1.03 g (69.1%), m.p. 202°-203° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. additionThe reaction mixture was then treated

Sources & evidence

ORD record
ord-f3cf09e4f816450a856771fcfbe22088
Source dataset
uspto-grants-1979_04
Patent number
US04150240

Reaction notes

Loading…