Triphenylphosphine → 1-[(Diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one

HRID 744015Notes

Reaction equation

HRID 744015 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([NH:12][NH:13][C:14]1[C:15](=[O:29])[N:16](O)[C:17]2[C:22]([N:23]=1)=[CH:21][CH:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=2)=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)(=O)C>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[N:23]2[C:22]3[C:17]([NH:16][C:15](=[O:29])[C:14]2=[N:13][N:12]=1)=[CH:18][C:19]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=3)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 194214493-[2-[(Diethoxyphosphoryl)acetyl]hydrazino]-1-hydroxy-7-trifluoromethylquinoxalin-2(1H)-one

Product 1

HCID 194214281-[(Diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-1-hydroxy-7-trifluoromethylquinoxalin-2(1H)-one (438 mg, 1 mmol) and triphenylphosphine (525 mg, 2 mmol) in 25 ml of glacial acetic acid was heated under reflux overnight (ca. 15 h). The mixture was evaporated to dryness, and the residue was flash chromatographed (SiO2) with dichloromethane to remove excess triphenylphosphine, then with ethyl acetate to remove triphenylphosphine oxide, and finally with 5% acetic acid in ethyl acetate to give 161 mg (40%) of the title compound. M.p. 224°-226° C., dec. (ethanol).

Workup

  1. temperatureunder reflux overnight (ca. 15 h)
  2. customThe mixture was evaporated to dryness
  3. customchromatographed (SiO2) with dichloromethane
  4. customto remove excess triphenylphosphine
  5. customwith ethyl acetate to remove triphenylphosphine oxide

Sources & evidence

ORD record
ord-c9e15b18de864f2cb7bc5edbd337cb50
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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