Triethylamine → 3-Chloro-6-cyano-2-[2-[(diethoxyphosphoryl)acetyl]hydrazino]quinoxaline

HRID 744016Notes

Reaction equation

HRID 744016 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].[Cl:13][C:14]1[C:15]([NH:26][NH2:27])=[N:16][C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]#[N:25])=[CH:19][CH:18]=2.C(N(CC)CC)C>O1CCCC1>[Cl:13][C:14]1[C:15]([NH:26][NH:27][C:10](=[O:11])[CH2:9][P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])=[N:16][C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]#[N:25])=[CH:19][CH:18]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10822542HCID 10822542, compoundHCID 194214233-Chloro-6-cyano-2-hydrazinoquinoxaline

Product 1

HCID 194214093-Chloro-6-cyano-2-[2-[(diethoxyphosphoryl)acetyl]hydrazino]quinoxaline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (diethoxyphosphoryl)acetyl chloride (2.15 g, 10 mmol) in 20 ml of dry tetrahydrofuran was added to a solution of 3-chloro-6-cyano-2-hydrazinoquinoxaline (2.0 g, 9 mmol) and dry triethylamine (1.4 ml, 10 mmol) in 100 ml of dry tetrahydrofuran. The mixture was stirred at room temperature overnight, and filtered. The filtrate was evaporated, and the title compound was isolated as a semisolid residue, which was used in the next step without further purification; 1H-NMR (DMSO-d6): δ 1.26 (t, 6H), 3.09 (d, 2H), 4.10 (quint, 4H), 7.71 (d, 1H), 7.97 (dd, 1H), 8.39 (d, 1H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b16fc9fb013c473d9bfb47687e8ebbe5
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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