Hydrochloric Acid → 5-[3-(4-Methoxyphenyl)propionyl]barbituric acid

HRID 1249674Notes

Reaction equation

HRID 1249674 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20](Cl)=[O:21])=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([CH:7]2[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][C:8]2=[O:9])=[O:21])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6211Barbituric AcidHCID 109324413-(4-Methoxyphenyl)propionyl chloride

Product 1

HCID 140406695-[3-(4-Methoxyphenyl)propionyl]barbituric acidYield 84.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of barbituric acid (6.4 g) in 48 ml of pyridine are added dropwise 11 g of 3-(4-methoxyphenyl)propionyl chloride and the mixture is stirred at room temperature for 18 hours. The reaction mixture is then poured into ice and acidified to pH=1 by adding 6 N hydrochloric acid. A solid precipitates, which is filtered and resuspended in methanol. The suspension is kept under stirring for 15 minutes, then the solid is recovered by filtration to give 12.2 g of the product, m.p. 248-250° C.

Workup

  1. additionThe reaction mixture is then poured into ice
  2. customA solid precipitates
  3. filtrationwhich is filtered
  4. stirringunder stirring for 15 minutes
  5. filtrationthe solid is recovered by filtration

Sources & evidence

ORD record
ord-3f8ba6930a59486f94a211254e6e2f1f
Source dataset
uspto-grants-2002_01
Patent number
US06335332B1

Reaction notes

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