5,5-Dibromobarbituric acid → HCID 23051859, compound

HRID 1651376Notes

Reaction equation

HRID 1651376 reaction equation
Br[C:2]1([Br:11])[C:7](=[O:8])NC(=O)NC1=O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21]C(=O)C)[CH:17]=[CH:18][CH:19]=1>CCOCC>[Br:11][CH2:2][C:7](=[O:8])/[CH:21]=[CH:20]/[C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=1

Participants

4

Reactant 2

HCID 948775,5-Dibromobarbituric acidHCID 1820074-(3-Methoxyphenyl)but-3-en-2-one

Product 1

HCID 23051859HCID 23051859, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 14.3 g (50 mmol) of 5,5-dibromobarbituric acid in 300 ml of ether was treated with 17.6 g (0.1 mol) of 4-(3-methoxyphenyl)-3-buten-2-one and the mixture was stirred at room temperature for 20 hours. The separated barbituric acid was filtered off. The filtrate was washed in succession with saturated sodium bicarbonate solution and with water. The organic phase was dried over sodium sulphate and concentrated. Flash chromatography of the residue on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1) yielded (E)-1-bromo-4-(3-methoxyphenyl)-3-buten-2-one as a yellow oil.

Workup

  1. filtrationThe separated barbituric acid was filtered off
  2. washThe filtrate was washed in succession with saturated sodium bicarbonate solution and with water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b2c17d8d099430692bb5dbd4a6aca7e
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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