Water → HCID 13318203, compound

HRID 485308Notes

Reaction equation

HRID 485308 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.C(N(CC)CC)C.O>N1C=CC=CC=1>[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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 68712882-Furancarboxaldehyde, oximeHCID 12946261HCID 12946261, compound

Product 1

HCID 13318203HCID 13318203, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine were dissolved 5.24 g (20 mmol) of ethyl 5-fluoro-6-acetoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate and 2.62 g (23.6 mmol) of (E)-furfuraldoxime, and 2.02 g (20 mmol) of triethylamine was added to the solution, followed by stirring at room temperature for 15 hours. The reaction solution was poured into 200 ml of ice-cooled water, and crystals precipitated were collected by filtration and washed with water. The crystals were dried under reduced pressure and recrystallized from ethanol to give 3.28 g of ethyl 5-fluoro-6-(E)-furfurylideneaminooxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate. m.p. 189°-190° C.

Workup

  1. additionwas added to the solution
  2. customprecipitated
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customThe crystals were dried under reduced pressure
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3c8452c7d0924ecd81821c455b465346
Source dataset
uspto-grants-1985_08
Patent number
US04536504

Reaction notes

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