Propan-2-yl 2-[(2-fluorophenyl)methylidene]-3-oxobutanoate → HCID 136364590, compound

HRID 2073626Notes

Reaction equation

HRID 2073626 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][CH:3]=1.[C:7]([C:10](=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24])[C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])(=O)[CH3:8]>C(#N)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:17]1[N:6]2[N:5]=[N:4][CH:3]=[C:2]2[NH:1][C:7]([CH3:8])=[C:10]1[C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 54405617Propan-2-yl 2-[(2-fluorophenyl)methylidene]-3-oxobutanoateHCID 178508070HCID 178508070, compound

Product 1

HCID 136364590HCID 136364590, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.34 g of 5-amino-1,2,3-triazole and 1.0 g of isopropyl α-acetyl-2-fluorocinnamate in 10 ml of acetonitrile is refluxed under heating for 4 hours. The solvent is distilled off under reduced pressure and the residue is crystallized from a mixture of diisopropyl ether and dichloromethane. The resulting crystals are recrystallized from a mixture of methanol, diisopropyl ether and hexane to give 0.3 g of 7-(2-fluorophenyl)-6-isopropoxycarbonyl-5-methyl-4,7-dihydro-1,2,3-triazolo[1,5-a]pyrimidine, melting at 137°-139° C., as colorless crystals.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 4 hours
  3. distillationThe solvent is distilled off under reduced pressure
  4. customthe residue is crystallized from a mixture of diisopropyl ether and dichloromethane
  5. customThe resulting crystals are recrystallized from a mixture of methanol, diisopropyl ether and hexane

Sources & evidence

ORD record
ord-44bced39f58344cd958d12f6afdc1b33
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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