Acetic Acid → 2,4(1H,3H)-Pyrimidinedione, dihydro-3-methyl-1-(4-(trifluoromethyl)phenyl)-

HRID 280107Notes

Reaction equation

HRID 280107 reaction equation
[CH3:1][NH:2][C:3]([N:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[CH2:6][CH2:7][C:8](O)=[O:9])=[O:4].Cl.C(O)(=O)C>O>[CH3:1][N:2]1[C:8](=[O:9])[CH2:7][CH2:6][N:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 23321818HCID 23321818, compound

Product 1

HCID 30636722,4(1H,3H)-Pyrimidinedione, dihydro-3-methyl-1-(4-(trifluoromethyl)phenyl)-Yield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At first, 4 g (0.014 moles) of N-(methylcarbamoyl)-N-(4-trifluoromethylphenyl)-β-alanine was added to a solution consisting of 45 ml of 6N-hydrochloric acid and 15 ml of acetic acid, and the mixture was refluxed with heating for 2 hours. After completion of the reaction, 50 ml of water was added thereto. The deposited crystals were recovered by filtration with suction and recrystallized from ethyl acetate-n-hexane, 3.38 g of the desired compound was obtained as colorless needle crystals having a melting point of 115°-117° C. (yield: 90.1%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. additionwas added
  4. filtrationThe deposited crystals were recovered by filtration with suction
  5. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-1cc9723014414bcc988713f1071c326f
Source dataset
uspto-grants-1986_05
Patent number
US04588729

Reaction notes

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