Ethylamine → 4-Ethylamino-[1,2,4]triazolo[4,3-a]quinoxaline

HRID 464286Notes

Reaction equation

HRID 464286 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:12]=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:15]([NH2:17])[CH3:16]>CN(C)C=O>[CH2:15]([NH:17][C:2]1[C:3]2[N:4]([CH:12]=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:16]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 11261184-Chloro[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 133857094-Ethylamino-[1,2,4]triazolo[4,3-a]quinoxalineYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 2.0 g. (0.01 mole) of 4-chloro-[1,2,4]triazolo[4,3-a]quinoxaline (the product of Example 2) in N,N-dimethylformamide (30 ml.) was saturated with monoethylamine gas and stirred at room temperature for 2 hours. Monoethylamine gas was again bubbled through the mixture and stirring was continued for 2 hours. The precipitate was removed by filtration and washed with N,N-dimethylformamide. Recrystallization from methanol afforded 680 mg. (32% yield) 4-ethylamino-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 254°-256° C. Mass spectrum: m/e, 213 (P).

Workup

  1. customMonoethylamine gas was again bubbled through the mixture
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. customThe precipitate was removed by filtration
  5. washwashed with N,N-dimethylformamide
  6. customRecrystallization from methanol
  7. customafforded 680 mg

Sources & evidence

ORD record
ord-44a7fdea810948d6b54a1d2b84d21fcf
Source dataset
uspto-grants-1985_10
Patent number
US04547501

Reaction notes

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