Diethylamine → 4-Diethylamino-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 1731952Notes

Reaction equation

HRID 1731952 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:14]([CH2:17][CH3:18])=[N:15][N:16]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20]>CN(C)C=O>[CH2:19]([N:21]([CH2:22][CH3:23])[C:2]1[C:3]2[N:4]([C:14]([CH2:17][CH3:18])=[N:15][N:16]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2)[CH3:20]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 133857264-Chloro-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 133857274-Diethylamino-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxalineYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline (520 mg., 0.002 mole) and 673 mg. (0.008 mole) of diethylamine in 10 ml. of N,N-dimethylformamide were stirred at room temperature overnight. The reaction mixture was poured over ice and the precipitate was separated by filtration, washed with water and air dried. Recrystallization from diethyl ether and petroleum ether than afforded 140 mg. (23% yield) of pure 4-diethylamino-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 135°-138° C.

Workup

  1. additionThe reaction mixture was poured over ice
  2. customthe precipitate was separated by filtration
  3. washwashed with water and air
  4. customdried
  5. customRecrystallization from diethyl ether and petroleum ether
  6. customthan afforded 140 mg

Sources & evidence

ORD record
ord-624e95c5ab3941cb8f238a811a84438d
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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