(+-)-2-Mercaptopropionic acid → Mezolidon

HRID 1388898Notes

Reaction equation

HRID 1388898 reaction equation
CO[C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[SH:13][CH:14]([CH3:18])[C:15](O)=[O:16].[C:19](=[O:22])([O-])[O-].[NH4+:23].[NH4+]>C1C=CC=CC=1>[CH3:19][O:22][C:8]1[CH:7]=[C:4]([CH:5]2[NH:23][C:15](=[O:16])[CH:14]([CH3:18])[S:13]2)[CH:3]=[CH:10][C:9]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 62326(+-)-2-Mercaptopropionic acidHCID 691752,4-DimethoxybenzaldehydeHCID 517111Ammonium Carbonate

Product 1

HCID 134071MezolidonYield 81%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 16.6 g of 2,4-dimethoxybenzaldehyde, 10.6 g of 2-mercaptopropionic acid and 6 g of ammonium carbonate in 250 ml of benzene was refluxed for 3 hours in a reaction vessel provided with a Dean-Stark apparatus at 80° C. while removing the distilled water. The crystals which separated out after cooling the reaction mixture were collected by filtration and recrystallized from hot benzene to obtain the object, colourless leaf-like crystals melting at 151° to 152.5° C. in an amount of 20.4 g corresponding to a yield of 81%.

Workup

  1. temperaturewas refluxed for 3 hours in a reaction vessel
  2. customprovided with a Dean-Stark apparatus at 80° C.
  3. customwhile removing the distilled water
  4. customThe crystals which separated out
  5. temperatureafter cooling the reaction mixture
  6. filtrationwere collected by filtration
  7. customrecrystallized from hot benzene

Sources & evidence

ORD record
ord-82d34c421d65427c9745161de64ef1a5
Source dataset
uspto-grants-1984_02
Patent number
US04434172

Reaction notes

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