Triethylamine → 7-cyano-1-propionyloxy-6-trifluoromethyl-quinoxaline-2,3(1H,4H)-dione

HRID 346141Notes

Reaction equation

HRID 346141 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][C:8](=[O:15])[C:9](=[O:14])[N:10]2[OH:13])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].C(N(CC)CC)C.[C:27](Cl)(=[O:30])[CH2:28][CH3:29]>O1CCCC1>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][C:8](=[O:15])[C:9](=[O:14])[N:10]2[O:13][C:27](=[O:30])[CH2:28][CH3:29])=[CH:5][C:4]=1[C:16]([F:19])([F:17])[F:18])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 199904087-cyano-1-propionyloxy-6-trifluoromethyl-quinoxaline-2,3(1H,4H)-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.4 g (1.48 mmol) 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline -2,3(1H,4H)-dione in 50 ml dry tetrahydrofuran was added 0.25 ml (1.82 mmol) dry triethylamine and 0.15 ml (1.72 mmol) propionyl chloride. The mixture was refluxed for 30 min., and then evaporated in vacuo. The residue was stirred with water to give 0.46 g (95%) 7-cyano-1-propionyloxy-6-trifluoromethyl-quinoxaline-2,3(1H,4H)-dione. M.p. 227° C. 1H-NMR (DMSO-d6): 8.37 (1H, s), 7.73 (1H, s), 4.5 (2H, q), 1.35 (3H, t).

Workup

  1. temperatureThe mixture was refluxed for 30 min.
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-dc241beffeab49b7bbbeab1ceed2e487
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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