4-Nitrophenyl trifluoroacetate → HCID 178524481, compound

HRID 436362

Reaction equation

HRID 436362 reaction equation
[NH:1]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[C:5](=[O:6])[NH:4][C:2]1=[O:3].FC(F)(F)C(O[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=O>N1C=CC=CC=1>[OH:3][C:2]1[N:4]=[C:5]([OH:6])[C:7]([C:9]([O:11][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[O:10])=[CH:8][N:1]=1

Participants

4

Reactant 2

HCID 695694-Nitrophenyl trifluoroacetateHCID 903011,2,3,4-Tetrahydro-2,4-dioxo-5-pyrimidinecarboxylic acid

Product 1

HCID 178524481HCID 178524481, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

Uracil-5-carboxylic acid (1.0 g) is dissolved in dry pyridine (20 ml) under heating. p-Nitrophenyl trifluroacetate (1.8 g) is added to the solution which is subsequently stirred at 45° C for 30 minutes. Then, the solution is concentrated to dryness under reduced pressure, and the cyrstals thus obtained are washed with chloroform and then acetone to give the active ester, i.e. p-nitrophenyl 2,4-dihydroxypyrimidine-5-carboxylate (1.16 g). M.P. 298°-299° C (decomp.).

Workup

  1. temperatureunder heating
  2. concentrationThen, the solution is concentrated to dryness under reduced pressure
  3. customthe cyrstals thus obtained
  4. washare washed with chloroform

Sources & evidence

ORD record
ord-973d09fdd4f848038325b3f993b5ec89
Source dataset
uspto-grants-1977_02
Patent number
US04008220

Linked notes

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