Water → HCID 13385734, compound

HRID 2412923Notes

Reaction equation

HRID 2412923 reaction equation
[NH2:1][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.[C:17](OC(=O)C)(=[O:19])[CH3:18].N1[CH:29]=[CH:28]C=CC=1.[OH2:30]>CN(C)C1C=CN=CC=1>[C:17]([N:1]([C:28](=[O:30])[CH3:29])[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)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 133857111-Ethyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amine

Product 1

HCID 13385734HCID 13385734, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture consisting of 5.5 g. (0.0258 mole) of 4-amino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline (the product of Example 14) and 25 g. (0.25 mole) of acetic anhydride (25 ml.) in 60 ml. of pyridine containing 100 mg. of p-dimethylaminopyridine was stirred at room temperature overnight (~18 hours). The resulting slurry was then filtered to remove the insolubles and the orange-red filtrate was thereafter evaporated under a high vacuum to give a dark gummy residue. Upon the addition of water, pinkish-white crystals were obtained and these were subsequently collected by means of suction filtration, washed with a copious amount of water and dried in vacuo at 50° C. to ultimately afford 2.9 g. (38%) of 4-diacetylamino-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 157°-159° C. Recrystallization of the latter material from ethyl acetate/diethyl ether then gave an analytically pure sample (m.p. 158°-160° C.). The pure product was further characterized by means of mass spectroscopy and nuclear magnetic resonance data, in addition to elemental analysis. Mass spectrum: m/e, 297 (P).

Workup

  1. filtrationThe resulting slurry was then filtered
  2. customto remove the insolubles
  3. customthe orange-red filtrate was thereafter evaporated under a high vacuum
  4. customto give a dark gummy residue
  5. custompinkish-white crystals were obtained
  6. filtrationthese were subsequently collected by means of suction filtration
  7. washwashed with a copious amount of water
  8. customdried in vacuo at 50° C. to ultimately afford 2.9 g
  9. customRecrystallization of the latter material from ethyl acetate/diethyl ether
  10. customthen gave an analytically pure sample (m.p. 158°-160° C.)
  11. additionThe pure product was further characterized by means of mass spectroscopy and nuclear magnetic resonance data, in addition to elemental analysis

Sources & evidence

ORD record
ord-5adb9d910aa64c029cbceb05148a9548
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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