Penicillamine → HCID 2825754, compound

HRID 867412Notes

Reaction equation

HRID 867412 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[CH3:10][S:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1>CO>[CH3:4][C:3]1([CH3:5])[S:6][CH:16]([C:15]2[CH:18]=[CH:19][C:12]([S:11][CH3:10])=[CH:13][CH:14]=2)[NH:1][C@H:2]1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 5852PenicillamineHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 2825754HCID 2825754, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 4.48 g (30 mmoles) of D-penicillamine and 3.99 ml (30 mmoles) of 4-methylmercaptobenzaldehyde in 90 ml of 30% aqueous methanol is stirred for 6 hours. The white solid precipitate is filtered out to give 8.26 g (97.1%) of the title product which can be recrystallized from methanol by adding water, m.p.: 150°-152° C., [α]D20 =+74.4° (c=0.516, dimethylsulphoxide).

Workup

  1. filtrationThe white solid precipitate is filtered out

Sources & evidence

ORD record
ord-505a62b1832645acb3a45e846b4039fa
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Reaction notes

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