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

HRID 2412907Notes

Reaction equation

HRID 2412907 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. Mass spectrum: m/e, 241 (P).

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-69cf0909fdf0440a9287fdc6214bf8c7
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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