Triethylamine → HCID 13309916, compound

HRID 325450Notes

Reaction equation

HRID 325450 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11](Cl)[C:10]=12)=[O:5])[CH3:2].[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[NH:21][NH2:22].C(N(CC)CC)C>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([NH:22][NH:21][C:20]([O:24][CH2:25][CH3:26])=[O:23])[C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 13309912HCID 13309912, compound

Product 1

HCID 13309916HCID 13309916, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloroimidazo[1,5-a]quinoxaline 3-carboxylic acid ethyl ester (5.5 g) in acetonitrile (120 ml) was added ethyl carbazate (9 g) and triethylamine (20 ml) with stirring. The mixture was refluxed for 18 hours, then evaporated under water aspirator vacuum to dryness. The residue was taken up in chloroform, washed with water, dried by magnesium sulfate, concentrated to a small volume, then put through a silica gel dry column (2% methanol in chloroform as eluant). From column the product was isolated as an off-white solid (4 g, 58% yield). Recrystallized from a mixture of chloroform and hexane, m.p. 126°-128° C.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customevaporated under water
  3. washwashed with water
  4. dry with materialdried by magnesium sulfate
  5. concentrationconcentrated to a small volume
  6. dry with materialdry column (2% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-1b6662337c3449c3b8ea7bd0b2001c94
Source dataset
uspto-grants-1984_04
Patent number
US04440929

Reaction notes

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