Phenobarbital → HCID 19975187, compound

HRID 2231622Notes

Reaction equation

HRID 2231622 reaction equation
[CH3:1][CH2:2][C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10](=[O:11])[NH:9][C:7](=[O:8])[NH:6]C1=O.[OH-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26]>CN(C)C=O>[C:25]([CH2:24][CH2:23][CH2:22][CH2:21][N:9]1[C:10](=[O:11])[C:3]([C:2]2[CH:1]=[CH:10][CH:3]=[CH:2][CH:1]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:6][C:7]1=[O:8])([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 4763PhenobarbitalHCID 14798Sodium HydroxideHCID 163685-Bromovaleric acid

Product 1

HCID 19975187HCID 19975187, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The DppE amide of 1-(4-carboxybutyl)-5-ethyl-5-phenyl barbituric acid (DPPE-phenobarbital) was prepared as outlined in FIG. 2. The sodium salt of phenobarbital (compound A) (2 mmoles) formed by treating phenobarbital with sodium hydroxide was reacted with the methyl ester of 5-bromovaleric acid (2.200 mmoles) in 5 ml of N,N-dimethyl formamide, for 4 hrs at 96° C., to form the methyl ester of 1-(4-carboxybutyl)-5-ethyl-5-phenyl barbiturate (compound B). The product was purified by column chromatography at a yield of about 77%.

Sources & evidence

ORD record
ord-8e77c1501bf44873af67467412e177b3
Source dataset
uspto-grants-1988_11
Patent number
US04783400

Reaction notes

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