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

HRID 66592

Reaction equation

HRID 66592 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. 1 N 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-80e63a5c163a4426b44a1d8406a739fb
Source dataset
uspto-grants-1982_08
Patent number
US04342771

Linked notes

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