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

HRID 464289Notes

Reaction equation

HRID 464289 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°-273° 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-5f132fce073e40769bd37b4017e76a4d
Source dataset
uspto-grants-1985_10
Patent number
US04547501

Reaction notes

Loading…