Sodium Carbonate → 2-(Chloromethyl)quinoxaline

HRID 610393Notes

Reaction equation

HRID 610393 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:18]Cl>C(Cl)(Cl)(Cl)Cl>[Cl:18][CH2:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 236862-MethylquinoxalineHCID 24526Chlorine2×

Product 1

HCID 137429242-(Chloromethyl)quinoxalineYield 23%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
68 °C

Procedure

2-Methylquinoxaline (8.94 g) was combined with 50 ml CCl4 and 6.5 g Na2CO3 in a 125 ml beaker. This was heated to 68° C. and then Cl2 was introduced via an inverted funnel so that the Cl2 was bubbled very slowly. This was continued for 1 hour and then the reaction mixture was cooled to 20° C. in an ice bath and partitioned between ether and saturated NaHCO3 solution. The ether was separated, dried over MgSO4, and concentrated to dryness. The residue was immediately flashed down a column packed with 20 cm of 32-63 micron silica gel (the column having a diameter of 8 cm) using 1:1 ether:hexane as eluant. After a 1 liter forerun, 250 ml fractions were collected. Fractions 3-5 were combined and concentrated to yield 2.58 g (23%) of title product as a yellow solid; tlc (3:7 ethyl acetate:CH2Cl2) Rf 0.65.

Workup

  1. customwas bubbled very slowly
  2. temperaturethe reaction mixture was cooled to 20° C. in an ice bath
  3. custompartitioned between ether and saturated NaHCO3 solution
  4. customThe ether was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customAfter a 1 liter forerun, 250 ml fractions were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6e1d23a7ecc74085b5602f883d607a49
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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