2-Methylaziridine → N-(2,3-dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-2-methylaziridine

HRID 1422240Notes

Reaction equation

HRID 1422240 reaction equation
Br[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.[CH3:20][CH:21]1[NH:23][CH2:22]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[CH3:17][O:16][C:7]1[C:6]([O:18][CH3:19])=[N:5][C:4]2[C:9](=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=2[CH2:2][N:23]2[CH2:22][CH:21]2[CH3:20])[N:8]=1

Participants

5

Reactant 3

HCID 63772-MethylaziridineHCID 2723671Tetrabutylammonium HydroxideHCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

Product 1

HCID 18706571N-(2,3-dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-2-methylaziridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.61 mmol) of 5-bromomethyl-2,3-dimethoxy-7-nitro-quinoxaline, 0.086 ml (2 equiv.) of propyleneimine and 0.295 ml (0.3 equiv.) of an aqueous 40% tetrabutylammonium hydroxide solution are stirred in 8 ml of dichloromethane for 20 hours at room temperature. The mixture is concentrated by evaporation and the residue is extracted with ethyl acetate and a 5% sodium carbonate solution. The combined organic phases are washed once with brine, dried over magnesium sulfate and concentrated by evaporation.

Workup

  1. concentrationThe mixture is concentrated by evaporation
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe combined organic phases are washed once with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f364f529c1054243a41dc138abe5b97d
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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