Dimethylamine → 1-ethyl-N,N-dimethyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amine

HRID 1731940Notes

Reaction equation

HRID 1731940 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:12]([CH2:15][CH3:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:17][NH:18][CH3:19]>CN(C)C=O>[CH3:17][N:18]([CH3:19])[C:2]1[C:3]2[N:4]([C:12]([CH2:15][CH3:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 133857064-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 8992951-ethyl-N,N-dimethyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amineYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-1-ethyl-[1,2,4]triazolo-[4,3-a]quinoxaline (1.2 g., 0.005 mole), the product of Example 4, and 676 mg. (0.015 mole) of anhydrous dimethylamine in N,N-dimethylformamide (50 ml.) were stirred at 0° C. for 30 minutes and at room temperature for 2 hours. The reaction mixture was poured over ice and stirred for 20 minutes. The precipitate which formed was separated by filtration, washed with water and air dried. Recrystallization from chloroform and then from chloroform/cyclohexane afforded 510 mg. (42% yield) of 4-dimethylamino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 155°-8° C.

Workup

  1. additionThe reaction mixture was poured over ice
  2. customThe precipitate which formed
  3. customwas separated by filtration
  4. washwashed with water and air
  5. customdried
  6. customRecrystallization from chloroform
  7. customfrom chloroform/cyclohexane afforded 510 mg

Sources & evidence

ORD record
ord-f438f51f835b4a998c6c758a71ce919f
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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