Ethylamine → N,1-Diethyl(1,2,4)triazolo(4,3-a)quinoxalin-4-amine

HRID 1731941Notes

Reaction equation

HRID 1731941 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl[C:5]1[C:6]2[N:7]([C:15]([CH2:18][CH3:19])=[N:16][N:17]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2>CN(C)C=O>[CH2:18]([C:15]1[N:7]2[C:8]3[C:13]([N:14]=[C:5]([NH:3][CH2:1][CH3:2])[C:6]2=[N:17][N:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:19]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 133857064-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 13385714N,1-Diethyl(1,2,4)triazolo(4,3-a)quinoxalin-4-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Monoethylamine 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 about 2 minutes. The clear solution was stirred at 0° C. for 30 minutes and at room temperature for 2 hours. The reaction mixture was next poured over ice and the precipitate was separated by filtration, washed with water and air dried. Recrystallization from ethanol then afforded 1.0 g. (83% yield) of pure 1-ethyl-4-ethylamino-[1,2,4]triazolo[4,3-a]quinoxaline as white solid (m.p. 235°-238° C.).

Workup

  1. additionThe reaction mixture was next poured over ice
  2. customthe precipitate was separated by filtration
  3. washwashed with water and air
  4. customdried
  5. customRecrystallization from ethanol
  6. customthen afforded 1.0 g

Sources & evidence

ORD record
ord-8a424e8d1bea446aa25ed9c6696d886d
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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