Tetrafluorophthalic anhydride → 5-Ethyl-1-phenyl-5-(tetrafluorophthalimido)barbituric acid

HRID 1020154Notes

Reaction equation

HRID 1020154 reaction equation
[NH2:1][C:2]1([CH2:17][CH3:18])[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[NH:4][C:3]1=[O:16].[F:19][C:20]1[C:21]([F:33])=[C:22]([F:32])[C:23]([F:31])=[C:24]2[C:29](=O)[O:28][C:26](=[O:27])[C:25]=12>C(O)(=O)C>[CH2:17]([C:2]1([N:1]2[C:29](=[O:28])[C:24]3=[C:23]([F:31])[C:22]([F:32])=[C:21]([F:33])[C:20]([F:19])=[C:25]3[C:26]2=[O:27])[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[NH:4][C:3]1=[O:16])[CH3:18]

Participants

4

Reactant 2

HCID 69545Tetrafluorophthalic anhydrideHCID 154249375-Amino-5-ethyl-1-phenylbarbituric acid

Product 1

HCID 99333935-Ethyl-1-phenyl-5-(tetrafluorophthalimido)barbituric acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of about 250 mg (about 1 mmol) of 5-amino-5-ethyl-1-phenylbarbituric acid, about 260 mg (about 1.2 mmol) of tetrafluorophthalic anhydride, and about 7 mL of acetic acid was refluxed for about 3 hours. The solvent was evaporated to dryness under reduced pressure of from about 200 to about 15 mbar. The residue was recrystallized from ethyl alcohol to yield about 270 mg 5-ethyl-1-phenyl-5-(tetrafluorophthalimido)barbituric acid (a 60% yield) having a melting point of about 218° to about 220° C.

Workup

  1. temperaturewas refluxed for about 3 hours
  2. customThe solvent was evaporated to dryness under reduced pressure of from about 200 to about 15 mbar
  3. customThe residue was recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-7d018a947d9a44d59d443296a3e00f66
Source dataset
uspto-grants-2014_05
Patent number
US08716315B2

Reaction notes

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