3-(2-(Diethoxyphosphorylacetyl)hydrazino)-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one → 3-[(Diethoxyphosphoryl)methyl]benzo[f]-1,2,4-triazolo[4,3-a]quinoxalin-12(11H)-one

HRID 744024Notes

Reaction equation

HRID 744024 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([NH:12][NH:13][C:14]1[C:23](=[O:24])[N:22](CC2C=CC(OC)=CC=2OC)[C:21]2[C:20]3[CH:36]=[CH:37][CH:38]=[CH:39][C:19]=3[CH:18]=[CH:17][C:16]=2[N:15]=1)=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>C(O)(=O)C>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[N:15]2[C:16]3[CH:17]=[CH:18][C:19]4[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=4[C:21]=3[NH:22][C:23](=[O:24])[C:14]2=[N:13][N:12]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 194214173-(2-(Diethoxyphosphorylacetyl)hydrazino)-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one

Product 1

HCID 194214063-[(Diethoxyphosphoryl)methyl]benzo[f]-1,2,4-triazolo[4,3-a]quinoxalin-12(11H)-oneYield 52.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(2-diethoxyphosphorylacetyl)hydrazino-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one (1.1 g crude product) and glacial acetic acid (40 ml) was heated under reflux for 12 h. The mixture was evaporated to dryness. The residue was recrystallized from isopropanol to give 400 mg of the title compound m.p. 195°-197° C. 1H-NMR (DMSO-d6): δ 1.18 (t, 6H), 4.08 (quint, 4H), 4.35 (d, 2H), 7.68 (m, 2H), 7.90 (d, 1H), 8.08 (m, 1H), 8.35 (d, 1H), 8.82 (m, 1H), 12.25 (s, 1H).

Workup

  1. temperatureunder reflux for 12 h
  2. customThe mixture was evaporated to dryness
  3. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-da2464d4f3424aad8d1497cfab540489
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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