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

HRID 1731939Notes

Reaction equation

HRID 1731939 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.

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-d7933a328423408e8d822bf0f11f42a4
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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