Sodium Carbonate → 2-(Chloromethyl)quinoxaline
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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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. 1H-NMR(CDCl3)delta(ppm): 4.86 (s, 2H), 7.74-7.78 (m, 2H), 8.02-8.16 (m, 2H), 9.0 (m, 1H).
Workup
- customwas bubbled very slowly
- temperaturethe reaction mixture was cooled to 20° C. in an ice bath
- custompartitioned between ether and saturated NaHCO3 solution
- customThe ether was separated
- dry with materialdried over MgSO4
- concentrationconcentrated to dryness
- customAfter a 1 liter forerun, 250 ml fractions were collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-268dcd866bec4dd798af22ee679cacba
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05059609
Reaction notes
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