Benzoyl Peroxide → 6-(chloromethyl)quinoxaline

HRID 412671Notes

Reaction equation

HRID 412671 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.[Cl:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C>[Cl:12][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 31398ChlorosuccinimideHCID 2425676-Methylquinoxaline

Product 1

HCID 101251116-(chloromethyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 500 ml flask, 6-methyl-quinoxaline (10 g, 69.4 mmol) was dissolved together with N-chlorosuccinimide (14 g, 105.3 mmol) and benzoyl peroxide (BP, 0.4 g, 1.65 mmol) in 240 g of acetonitrile. The flask was connected to a reflux-condenser and the solution was refluxed for 6 hours followed by another addition of 0.1 g of benzoyl peroxide. Reflux was then continued for another 6 hours.

Workup

  1. customThe flask was connected to a reflux-condenser
  2. temperaturethe solution was refluxed for 6 hours
  3. temperatureReflux

Sources & evidence

ORD record
ord-2ac37084b32c4c2fb37b8486e49005ec
Source dataset
uspto-grants-2003_05
Patent number
US06562972B1

Reaction notes

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