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

HRID 580552

Reaction equation

HRID 580552 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH:13]1[C:21](=[O:22])[C:19](=[O:20])[C:17](=[O:18])[NH:16][C:14]1=[O:15].Cl>C(O)C>[OH:20][C:19]1([C:8]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]=[CH:10][CH:9]=2)[C:17](=[O:18])[NH:16][C:14](=[O:15])[NH:13][C:21]1=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 124801-PhenylpyrroleHCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrate2×

Product 1

HCID 132828945-Hydroxy-5-(1-phenyl-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrioneYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Phenylpyrrole (1.4 g., 0.01 mole), alloxan hydrate (1.6 g., 0.01 mole) and 50 ml. of ethanol were combined and refluxed for 15 minutes. No reaction was noted by tlc. 1N Hydrochloric acid (10 ml., 0.01 mole) was added and the acidified mixture refluxed for 15 minutes. Incomplete reaction was noted by tlc. A second portion of alloxan hydrate (1.6 g., 0.01 mole) was added and the mixture refluxed another 15 minutes, cooled and evaporated to dryness. Trituration of the residue with water gave title product [2.3 g.; m/e 285; m.p. 232°-234° C. (dec); Rf 0.3 (1:1 ethyl acetate:hexane)].

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperaturethe acidified mixture refluxed for 15 minutes
  3. customIncomplete reaction
  4. temperaturethe mixture refluxed another 15 minutes
  5. temperaturecooled
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-81d3663c0c9b4ed2bbd9d0b8550f011f
Source dataset
uspto-grants-1988_06
Patent number
US04753956

Linked notes

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