Potassium Nitrate → 1-[(Diethoxyphosphoryl)methyl]-8-nitro-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one

HRID 744018Notes

Reaction equation

HRID 744018 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH2:6]([O:8][P:9]([CH2:14][C:15]1[N:19]2[C:20]3[C:25]([NH:26][C:27](=[O:28])[C:18]2=[N:17][N:16]=1)=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][CH:21]=3)([O:11][CH2:12][CH3:13])=[O:10])[CH3:7]>S(=O)(=O)(O)O>[CH2:12]([O:11][P:9]([CH2:14][C:15]1[N:19]2[C:20]3[C:25]([NH:26][C:27](=[O:28])[C:18]2=[N:17][N:16]=1)=[CH:24][C:23]([C:29]([F:30])([F:32])[F:31])=[C:22]([N+:1]([O-:4])=[O:2])[CH:21]=3)([O:8][CH2:6][CH3:7])=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 194214281-[(Diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one

Product 1

HCID 194214311-[(Diethoxyphosphoryl)methyl]-8-nitro-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-oneYield 79.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Powdered potassium nitrate (1.82 g, 18 mmol) was added to a stirred solution of 1-[(diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo [4,3-a]quinoxalin-4(5H)-one (3.7 g, 9.15 mmol) in 50 ml of conc. sulfuric acid at 0° C. The mixture was stirred at room temperature overnight, and quenched in ice/water (300 g). The aqueous phase was extracted with ethyl acetate (5×100 ml), and the combined organic extracts were dried with anhydrous sodium sulfate, and evaporated. The residue was triturated with ether to give 3.25 g (79%) of the title compound, m.p. 222°-228° C.; 1H-NMR (DMSO-d6): δ 1.20 (t, 6H), 4.10 (quint, 4H), 4.39 (d, 2H), 7.88 (s, 1H), 8.96 (s, 1H), 12.67 (br s, 1H).

Workup

  1. customquenched in ice/water (300 g)
  2. extractionThe aqueous phase was extracted with ethyl acetate (5×100 ml)
  3. dry with materialthe combined organic extracts were dried with anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-7066b27d4a5d4ee79f77c7b338b58eef
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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