Triethylamine → N,N-dihexyl-1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxamide

HRID 844520Notes

Reaction equation

HRID 844520 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18](O)=[O:19])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:35]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>O1CCCC1>[CH2:42]([N:41]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:18]([C:10]1[C:9](=[O:21])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[C:12]([N:11]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:19])[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8920DihexylamineHCID 10928Ethyl chloroformateHCID 154617741-Benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acid

Product 1

HCID 15461770N,N-dihexyl-1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 30 ml of tetrahydrofuran were dissolved 0.50 g of 1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acid and 0.87 ml of triethylamine, and after cooling to —40° C., 0.19 ml of ethyl chlorocarbonate was added dropwise over 5 minutes. After stirring at −40° C. for 10 minutes, 0.46 ml of dihexylamine was added dropwise over 5 minutes. After stirring at −40° C. for an hour, the temperature was raised to room temperature over an hour, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue, after addition of ethyl acetate, was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; chloroform) and recrystallized from hexane to give 0.53 g of N,N-dihexyl-1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxamide.

Workup

  1. temperatureafter cooling to —40° C.
  2. stirringAfter stirring at −40° C. for an hour
  3. temperaturethe temperature was raised to room temperature over an hour
  4. stirringby stirring at room temperature overnight
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionthe residue, after addition of ethyl acetate
  7. washwas washed with water, 1N hydrochloric acid
  8. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  9. customAfter removal of the drying agent
  10. filtrationby filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; chloroform)
  13. customrecrystallized from hexane

Sources & evidence

ORD record
ord-18503b74255147c5b6fe5f43c0b05eb9
Source dataset
uspto-grants-2002_04
Patent number
US06380384B1

Reaction notes

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