HCID 5354160, compound → ethyl 5-fluoro-6-(E)-furfurylideneaminooxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate

HRID 485307Notes

Reaction equation

[F:1][C:2]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]([O:8]C(=O)C)[NH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13].[CH:19](=[N:25]/O)/[C:20]1[O:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1.CC(C)=O>[F:1][C:2]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]([O:8]/[N:25]=[CH:19]\[C:20]2[O:24][CH:23]=[CH:22][CH:21]=2)[NH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

In 450 ml of pyridine-acetone (pyridine:acetone=2:1) were dissolved 131 g (0.5 mol) of ethyl 5-fluoro-6-acetoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate and 66.5 g (0.6 mol) of (Z)-furfuraldoxime, and the solution was stirred at 60° C. for 15 hours. The solvent was evaporated under reduced pressure, and the residual oily material was poured into 3 l of ice-cooled water, and crystals precipitated were collected by filtration. The crystals were washed with water (500 ml×2), dried under reduced pressure and recrystallized from ethanol and then from ethyl acetate-hexane (7:3) to yield 63.5 g of ethyl 5-fluoro-6-(Z)-furfurylideneaminooxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5carboxylate. m.p. 152°-153° C.

Workup

customThe solvent was evaporated under reduced pressure
additionthe residual oily material was poured into 3 l of ice-
temperaturecooled water, and crystals
customprecipitated
filtrationwere collected by filtration
washThe crystals were washed with water (500 ml×2)
customdried under reduced pressure
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-96c9b1cdc9ac4d13b18b81a123f0c7ba
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04536504

Reaction notes

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