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

HRID 2412919Notes

Reaction equation

HRID 2412919 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 then 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. Mass spectrum: m/e, 299 (P).

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. customthen afforded 140 mg

Sources & evidence

ORD record
ord-f48505be147d455e94386195e4515a91
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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