Diethylamine → HCID 13385730, compound

HRID 2412922Notes

Reaction equation

HRID 2412922 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][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:12]([C:15]([F:18])([F:17])[F:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:20]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 14280609HCID 14280609, compound

Product 1

HCID 13385730HCID 13385730, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 700 mg. (0.0025 mole) of 4-chloro-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxaline (prepared as described above) and 560 mg. (0.0075 mole) of diethylamine (0.8 ml.) in 10 ml. of N,N-dimethylformamide was stirred at room temperature overnight and then poured over ice. The resulting mixture was then filtered and the recovered solid product washed with water and then dissolved in ethyl acetate. The latter organic solution was next washed with saturated brine and dried over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there was ultimately obtained a light yellow solid which after recrystallization from diethyl ether gave pure 4-diethylamino-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxaline. The yield of the first crop melting at 155°-157° C. amounted to 260 mg. (34%), while the yield of the second crop melting at 153°-156° C. amounted to 170 mg. (22%).

Workup

  1. additionpoured over ice
  2. filtrationThe resulting mixture was then filtered
  3. washthe recovered solid product washed with water
  4. dissolutiondissolved in ethyl acetate
  5. washnext washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby means of filtration
  9. customthe solvent by means of evaporation under reduced pressure, there
  10. customwas ultimately obtained a light yellow solid which
  11. customafter recrystallization from diethyl ether

Sources & evidence

ORD record
ord-329f270cdb19449482e1880c9d6e118f
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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