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

HRID 1731946Notes

Reaction equation

HRID 1731946 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-6e6295f455ec49c2b919e62d4e8b08dd
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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