Diethylamine → 4-Diethylamino-1-n-propyl-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 2412913Notes

Reaction equation

HRID 2412913 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:12]([CH2:15][CH2:16][CH3:17])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19]>CN(C)C=O>[CH2:18]([N:20]([CH2:21][CH3:22])[C:2]1[C:3]2[N:4]([C:12]([CH2:15][CH2:16][CH3:17])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:19]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 133857074-Chloro-1-propyl[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 133857194-Diethylamino-1-n-propyl-[1,2,4]triazolo[4,3-a]quinoxalineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-1-n-propyl-[1,2,4]-triazolo[4,3-a]quinoxaline (1.23 g., 0.005 mole), the product of Example 5, and 1.1 g. (0.015 mole) of diethylamine in N,N-dimethylformamide (15 ml.) were stirred at room temperature for 2 hours. The reaction mixture was then poured over ice. The precipitate was removed by filtration, washed with water and air dried. Recrystallization (twice) from ethanol/water afforded 1.1 g. (78% yield) of pure 4-diethylamino-1-n-propyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 92°-94° C. Mass spectrum: m/e, 283 (P).

Workup

  1. additionThe reaction mixture was then poured over ice
  2. customThe precipitate was removed by filtration
  3. washwashed with water and air
  4. customdried
  5. customRecrystallization (twice) from ethanol/water
  6. customafforded 1.1 g

Sources & evidence

ORD record
ord-757fe35ff536444b9cf9d9b03c43e85e
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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