Acetaldehyde → Dimethyl N-(7-Nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-alpha-aminoethylphosphonate

HRID 1953777Notes

Reaction equation

HRID 1953777 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2.S([O-])([O-])(=O)=O.[Mg+2].C(=O)([O-])[O-].[K+].[K+].C(=O)C.C(N([CH2:40][CH3:41])CC)C.[P:42]([O-:47])([O:45][CH3:46])[O:43][CH3:44].C[Si](C)(C)Cl>ClCCl.O>[N+:13]([C:11]1[CH:10]=[C:9]2[C:4]([N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2)=[C:3]([CH2:2][NH:1][CH:40]([P:42](=[O:47])([O:45][CH3:46])[O:43][CH3:44])[CH3:41])[CH:12]=1)([O-:15])=[O:14]

Participants

10

Reactant 7

HCID 177AcetaldehydeHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 179152965-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxalineHCID 21884954Dimethylphosphite

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

500 mg (1.9 mmol) of 5-aminomethyl-7-nitro-2,3-dimethoxyquinoxaline, 834 mg (3.7 eq.) of magnesium sulfate, 335 mg (1.3 eq.) of potassium carbonate and 0.214 ml (2 eq.) of acetaldehyde are stirred at room temperature for 7 hours in 15 ml of dichloromethane. The reaction mixture is filtered off and the filtrate is evaporated. A solution of 0.32 ml (1.2 eq.) of triethylamine, 0.182 ml of dimethyl phosphite and 0.36 ml (1.5 eq.) of trimethylchlorosilane in 10 ml of dichloromethane is stirred at 0° for one hour, and the residue is added to 10 ml of dichloromethane and stirred for 14 hours. Water is added to the reaction mixture and the organic phase is separated off. The aqueous phase is extracted twice with dichloromethane and the combined organic phases are dried over magnesium sulfate. The title compound is obtained as a yellow resin after evaporation of the solvent.

Workup

  1. filtrationThe reaction mixture is filtered off
  2. customthe filtrate is evaporated
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted twice with dichloromethane
  5. dry with materialthe combined organic phases are dried over magnesium sulfate

Sources & evidence

ORD record
ord-bc2cd44919154f3abf6da06e70be51a8
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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