Iodoethane → dimethyl N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-alpha-(ethylamino)ethylphosphonate

HRID 1953780Notes

Reaction equation

HRID 1953780 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[N:11]2)=[C:6]([CH2:18][NH:19][CH:20]([P:22](=[O:27])([O:25][CH3:26])[O:23][CH3:24])[CH3:21])[CH:5]=1)([O-:3])=[O:2].[CH2:28](I)[CH3:29].C(N(C(C)C)CC)(C)C>C(#N)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[N:11]2)=[C:6]([CH2:18][N:19]([CH2:28][CH3:29])[CH:20]([P:22](=[O:27])([O:23][CH3:24])[O:25][CH3:26])[CH3:21])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 23297975Dimethyl N-(7-Nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-alpha-aminoethylphosphonate

Product 1

HCID 23298022dimethyl N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-alpha-(ethylamino)ethylphosphonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

300 mg (0.75 mmol) of dimethyl N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-α-aminoethylphosphonate, 0.482 ml (8 eq.) of ethyl iodide and 1.4 ml (11 eq.) of diisopropylethylamine are stirred at 700 for 24 hours in 10 ml of acetonitrile. The reaction mixture is evaporated and the residue is stirred in diethyl ether. The solid is filtered off, washed with diethyl ether and the filtrate is evaporated. The title compound is obtained as a brownish oil.

Workup

  1. customThe reaction mixture is evaporated
  2. filtrationThe solid is filtered off
  3. washwashed with diethyl ether
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-a2966ee69d99414abdb20a20e52a4394
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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