Pyridine → 5-(3-Methyl-2-butenyl)-5-trifluoromethylbarbituric acid

HRID 1657960Notes

Reaction equation

[NH2:1][C:2]([NH2:4])=[O:3].N1C=CC=CC=1.[CH3:11][C:12]([CH3:26])=[CH:13][CH2:14][C:15]([C:22]([F:25])([F:24])[F:23])([C:19](F)=[O:20])[C:16](F)=[O:17]>C(COC)OC>[CH3:11][C:12]([CH3:26])=[CH:13][CH2:14][C:15]1([C:22]([F:23])([F:24])[F:25])[C:16](=[O:17])[NH:4][C:2](=[O:3])[NH:1][C:19]1=[O:20]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 0.96 g (0.016 mol) of urea, 2.45 g (0.031 mol) of pyridine and 20 ml of glyme was stirred at 25°C while 3.8 g (0.0155 mol) of (3-methyl-2-butenyl)trifluoromethylmalonyl fluoride in 10 ml of glyme was added rapidly. The mixture was stirred overnight, heated for 10 minutes at 70°C, and evaporated to a viscous residue. Trituration of the residue with 20 ml of water gave 2.7 g (66%) of 5-(3-methyl-2-butenyl)-5-trifluoromethylbarbituric acid, mp 150°-153°C. A sample for analysis was recrystallized from water, mp 154°-155°C; ir (KBr): 3.04 and 3.18 (NH), 3.32, 3.39 and 3.44 (CH), 5.63 and 5.81 (C=O), and 8-8.5 μ (CF). Raman ir spectrum showed C=C at 5.95 μ; nmr ((CD3)2CO): 1H at ca. 9.0 (very broad (partly exchanged into acetone-d6), 2, NH), 5.03 (triplet, JHH = 7.7 Hz, 1, =CH), 3.07 (doublet, JHH = 7.7 Hz, 2, =CCH2), 1.69 and 1.67 ppm (singlets, 6, =CCH3); 19F at -69.0 ppm (singlet, CF3).

Workup

additionwas added rapidly
customevaporated to a viscous residue

Sources & evidence

ORD record: ord-ed59b668dd28442a9627933da7390adc
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03962325

Reaction notes

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