Hydrogen Bromide → 5-Bromo-5-octylbarbituric acid

HRID 993071Notes

Reaction equation

HRID 993071 reaction equation
[CH2:1]([CH:9]1[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[BrH:18].BrBr>O>[Br:18][C:9]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]1=[O:17]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 260794Octyl barbituric acid

Product 1

HCID 184088325-Bromo-5-octylbarbituric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 5-octylbarbituric Acid (20 g) in 120 ml of water, cooled at 0-5° C., are added 12 ml of 48% hydrobromic acid and successively are dropped 4.72 ml of bromine. Ater 2 hours under stirring, the white solid which separated is recovered by filtration, washed with water and partitioned between 200 ml of diethyl ether and 100 ml of water. The aqueous phase is extracted with additional 50 ml of diethyl ether. The pooled organic phases are washed with 75 ml of saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. 25.8 g of the product as white solid are obtained.

Workup

  1. customthe white solid which separated
  2. filtrationis recovered by filtration
  3. washwashed with water
  4. custompartitioned between 200 ml of diethyl ether and 100 ml of water
  5. extractionThe aqueous phase is extracted with additional 50 ml of diethyl ether
  6. washThe pooled organic phases are washed with 75 ml of saturated aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2fc0ea8d86bb4c37af4ccdb34c80ccfb
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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