Benzoyl Peroxide → 5-Bromo-5-[3-(4-methoxyphenyl)propyl]barbituric acid

HRID 993053Notes

Reaction equation

HRID 993053 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14][C:13]2=[O:20])=[CH:5][CH:4]=1.[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][C:12]1([CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:13](=[O:20])[NH:14][C:15](=[O:19])[NH:16][C:17]1=[O:18]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 140406705-[3-(4-Methoxyphenyl)propyl]barbituric acid

Product 1

HCID 184086795-Bromo-5-[3-(4-methoxyphenyl)propyl]barbituric acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-[3-(4-Methoxyphenyl)propyl]barbituric Acid (2.5 g), N-bromosuccinimide (2 g) and dibenzoyl peroxide (catalytic amount) in 110 ml of carbon tetrachloride is refluxed for about 1 hour, then the solid which separated is filtered. The solid is redissolved in ethyl acetate and filtered through a silica gel cake in order to eliminate the succinimide residue. The organic phase is then concentrated to dryness and the residue is crystallized from diethylether/carbon tetrachloride mixture. A pale yellow solid separates which is filtered and dried under vacuum at 60° C. to give 2.8 g of the product, m.p. 113-114° C.

Workup

  1. temperatureis refluxed for about 1 hour
  2. customthe solid which separated
  3. filtrationis filtered
  4. dissolutionThe solid is redissolved in ethyl acetate
  5. filtrationfiltered through a silica gel cake in order
  6. concentrationThe organic phase is then concentrated to dryness
  7. customthe residue is crystallized from diethylether/carbon tetrachloride mixture
  8. filtrationA pale yellow solid separates which is filtered
  9. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-398e02aef0a64d7bae314805dffbff4a
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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