Hydrochloric Acid → 5-Hydroxy-5-(5-bromo-3-indolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

HRID 1194020

Reaction equation

HRID 1194020 reaction equation
O.[NH:2]1[C:10](=[O:11])[C:8](=[O:9])[C:6](=[O:7])[NH:5][C:3]1=[O:4].[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2.Cl>C(O)C>[OH:9][C:8]1([C:16]2[C:15]3[C:19](=[CH:20][CH:21]=[C:13]([Br:12])[CH:14]=3)[NH:18][CH:17]=2)[C:6](=[O:7])[NH:5][C:3](=[O:4])[NH:2][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrateHCID 249055-Bromoindole

Product 1

HCID 132828955-Hydroxy-5-(5-bromo-3-indolyl)-2,4,6-(1H,3H,5H)pyrimidinetrioneYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alloxan hydrate (1.6 g., 0.01 mole) was dissolved in 40 ml. of ethanol by heating. 5-Bromoindole (1.96 g., 0.01 mole) was added and heating near reflux continued for 15 minutes. Tlc did not indicate that reaction had occured. 1N Hydrochloric acid (10 ml.) was then added while maintaining the reaction near reflux. After 10 minutes, the reaction was concentrated to wet solids. Trituration of these wet solids with water gave the title product [3.17 g., m.p. >250° C.; Rf 0.45 (1:1 ethyl acetate:hexane/5% acetic acid); Rf 0.3 (1:5 ethyl acetate:hexane/5% acetic acid)].

Workup

  1. temperatureheating
  2. temperaturenear reflux
  3. customTlc did not indicate that reaction
  4. temperaturewhile maintaining
  5. customthe reaction
  6. temperaturenear reflux
  7. waitAfter 10 minutes
  8. concentrationthe reaction was concentrated to wet solids

Sources & evidence

ORD record
ord-a3ea5b7384314b0f8cae23353f17caef
Source dataset
uspto-grants-1989_03
Patent number
US04812471

Linked notes

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