Methylamine → 4-Methylamino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 2412906Notes

Reaction equation

HRID 2412906 reaction equation
[CH3:1][NH2:2].Cl[C:4]1[C:5]2[N:6]([C:14]([CH2:17][CH3:18])=[N:15][N:16]=2)[C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2>CN(C)C=O>[CH3:1][NH:2][C:4]1[C:5]2[N:6]([C:14]([CH2:17][CH3:18])=[N:15][N:16]=2)[C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 133857064-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 133857124-Methylamino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalineYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Monomethylamine gas was bubbled through a solution of 4-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline (1.2 g., 0.005 mole), the product of Example 4, in N,N-dimethylformamide (50 ml.) at 0° C. for 2 minutes. The reaction mixture was stirred at 0° C. for 30 minutes, at room temperature for 2 hours, and then poured over ice and stirred another 20 minutes. The precipitate which formed was separated by filtration, washed with water and air dried. Recrystallization from ethanol then afforded 1.0 g. (88% yield) of 4-methylamino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 271°-3° C. Mass spectrum: m/e, 227 (P).

Workup

  1. additionpoured over ice
  2. stirringstirred another 20 minutes
  3. customThe precipitate which formed
  4. customwas separated by filtration
  5. washwashed with water and air
  6. customdried
  7. customRecrystallization from ethanol
  8. customthen afforded 1.0 g

Sources & evidence

ORD record
ord-5eb8182de32343c1a73080f0e910612f
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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