Pyridine → Ethyl N-(6,7-dichloro-2-methoxyquinoxalin-3-yl)carbamate

HRID 1878283Notes

Reaction equation

HRID 1878283 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[C:7]([Cl:14])[CH:8]=2)[N:3]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1C=CC=CC=1>ClCCl>[Cl:15][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[Cl:14])[N:10]=[C:11]([O:12][CH3:13])[C:2]([NH:1][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[N:3]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 692433492-Amino-6,7-dichloro-3-methoxyquinoxaline

Product 1

HCID 69243293Ethyl N-(6,7-dichloro-2-methoxyquinoxalin-3-yl)carbamateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-6,7-dichloro-3-methoxyquinoxaline (1.16 g, 4.75 mmol) and ethyl chloroformate (1.03 g, 9.50 mmol) were dissolved in dichloromethane (50 ml) at room temperature and thereto pyridine (751 mg, 9.50 mmol) was added. The mixture was stirred at room temperature for 24 hours and concentrated under the reduced pressure to remove the solvent, and purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (2:1) mixture and concentration gave 1.29 g of the titled compound (yield, 86%).

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. custompurified by SiO2 column chromatography
  4. extractionExtraction of the residue
  5. concentrationwith a n-hexane:ethyl acetate (2:1) mixture and concentration

Sources & evidence

ORD record
ord-882ee2faa6a347c5b2f867c1bbfcd2cb
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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