Triethylamine → 3-(2-(Diethoxyphosphorylacetyl)hydrazino)-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one

HRID 744023Notes

Reaction equation

HRID 744023 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10](Cl)=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH3:13][O:14][C:15]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:16]=1[CH2:17][N:18]1[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[CH:24]=[CH:23][C:22]=2[N:21]=[C:20]([NH:32][NH2:33])[C:19]1=[O:34].C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:3][P:4]([CH2:9][C:10]([NH:33][NH:32][C:20]1[C:19](=[O:34])[N:18]([CH2:17][C:16]2[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[CH:38][C:15]=2[O:14][CH3:13])[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[CH:24]=[CH:23][C:22]=2[N:21]=1)=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10822542HCID 10822542, compoundHCID 194214421-(2,4-dimethoxybenzyl)-3-hydrazinobenzo[f]quinoxalin-2(1H)-one

Product 1

HCID 194214173-(2-(Diethoxyphosphorylacetyl)hydrazino)-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-oneYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (diethoxyphosphoryl)acetyl chloride (480 mg, 2.2 mmol) in dry tetrahydrofuran (10 ml) was added to a mixture of 1-(2,4-dimethoxybenzyl)-3-hydrazinobenzo[f]quinoxalin-2(1H)-one (750 mg, 2 mmol) and dry triethylamine (220 mg, 2.2 mmol) in dry tetrahydrofuran (40 ml). The mixture was stirred at room temperature for 1.5 h and filtered. The filtrate was evaporated to give 1.1 g of the title compound as a crude product.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-66e67120e3374b00a5849a7fb99de45e
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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