Benzaldehyde → HCID 2825757, compound

HRID 2216430Notes

Reaction equation

HRID 2216430 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C@@H:10]([C:15]([OH:17])=[O:16])[C:11]([SH:14])([CH3:13])[CH3:12].[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(O)C.O>[C:18]([N:9]1[C@@H:10]([C:15]([OH:17])=[O:16])[C:11]([CH3:13])([CH3:12])[S:14][C@H:1]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5852PenicillamineHCID 7918Acetic Anhydride

Product 1

HCID 2825757HCID 2825757, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of benzaldehyde (102 ml, 1.01 mol) in ethanol (300 ml) was added to a solution of D-penicillamine (150 g, 1.01 mol) in water (900 ml) at room temperature. The mixture was stirred at room temperature for 15 minutes and under ice-cooling for 1.5 hours, and then the precipitated crystals were filtered off and dried. Acetic anhydride (480 ml, 5.05 mol) was added dropwise to a solution of the obtained crystals in water (700 ml) at 60° C. over 15 minutes. The mixture was stirred at the temperature for 15 minutes, then at room temperature for 15 minutes and under ice-cooling for 1.5 hours, and the precipitated crystals were filtered off and dried to give 252.3 g (89%) of the target compound.

Workup

  1. temperaturecooling for 1.5 hours
  2. filtrationthe precipitated crystals were filtered off
  3. customdried
  4. stirringThe mixture was stirred at the temperature for 15 minutes
  5. waitat room temperature for 15 minutes
  6. temperatureunder ice-cooling for 1.5 hours
  7. filtrationthe precipitated crystals were filtered off
  8. customdried

Sources & evidence

ORD record
ord-0a3be4f3e20c49189335732640fc5dc6
Source dataset
uspto-grants-2006_09
Patent number
US07112598B2

Reaction notes

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