Triethylamine → 4-[3-(2-Quinoxaloylamino)propylthio]pyridine

HRID 6173Notes

Reaction equation

HRID 6173 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[C:31](Cl)=[O:32]>C(Cl)Cl>[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[C:31]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734681Quinoxaline-2-carbonyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 190791224-[3-(2-Quinoxaloylamino)propylthio]pyridineYield 48.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.30 g (17.8 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 8.68 ml (62.3 mmol) of triethylamine in 200 ml of methylene chloride, 3.43 g (17.8 mmol) of 2-quinoxaloyl chloride was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate and water, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) and recrystallization (solvent: ethyl acetate-ether) to give 2.82 g of the desired compound (48.9% yield, white crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate) and recrystallization (solvent: ethyl acetate-ether)

Sources & evidence

ORD record
ord-d1d9d0850f644a438eba335e3ea1f8ab
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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