Hydrogen Bromide → 5-Bromo-5-(4'-phenoxyphenyl)barbituric acid

HRID 993080Notes

Reaction equation

HRID 993080 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16][C:15]2=[O:22])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:23].BrBr>O>[Br:23][C:14]1([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)[C:15](=[O:22])[NH:16][C:17](=[O:21])[NH:18][C:19]1=[O:20]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 116737785-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trione

Product 1

HCID 227322335-Bromo-5-(4'-phenoxyphenyl)barbituric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-(4′-phenoxyphenyl)barbituric Acid (48 mg) in 0.23 ml of water, cooled at 0° C. and under stirring, are added 23 ml of 48% hydrobromic acid and successively 9 μl of bromine. After 2 hours at room temperature additional 9 μl of bromine are added and stirring is continued for 2 hours. The suspended solid is then filtered and washed with water, to give, after drying under vacuum at 60° C., 57 mg of the product, m.p. 125-127° C.

Workup

  1. stirringstirring
  2. filtrationThe suspended solid is then filtered
  3. washwashed with water
  4. customto give
  5. customafter drying under vacuum at 60° C.

Sources & evidence

ORD record
ord-899d979c058943989dad4a8cba3bcd22
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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