Methyl iodide → 4-(8-Bromodibenz[b,f]oxepin-10-yl)-1-methylpyridinium iodide

HRID 1982160Notes

Reaction equation

HRID 1982160 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[C:7]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:6]=2[CH:22]=1.[CH3:23][I:24]>C(#N)C>[I-:24].[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[C:7]([C:16]3[CH:17]=[CH:18][N+:19]([CH3:23])=[CH:20][CH:21]=3)[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 136086134-(8-Bromodibenz[b,f]oxepin-10-yl)pyridine

Product 1

HCID 233174974-(8-Bromodibenz[b,f]oxepin-10-yl)-1-methylpyridinium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(8-bromodibenz[b,f]oxepin-10-yl)pyridine (2.0 g) in acetonitrile (30 ml) containing methyl iodide (1.1 ml) was stirred under reflux in an argon atmosphere for ninety minutes. During this time the starting material gradually dissolved and a yellow solid began to precipitate from solution. The mixture was cooled to -10° and the solids were collected by filtration and were washed in turn with cold acetonitrile and ether to give 2.7 g of 4-(8-bromo-dibenz[b,f]oxepin-10-yl)-1-methylpyridinium iodide.

Workup

  1. temperatureunder reflux in an argon atmosphere for ninety minutes
  2. dissolutionDuring this time the starting material gradually dissolved
  3. customto precipitate from solution
  4. temperatureThe mixture was cooled to -10°
  5. filtrationthe solids were collected by filtration
  6. washwere washed in turn with cold acetonitrile and ether

Sources & evidence

ORD record
ord-0fe54f9a9f9748aaa1bece183eec0f55
Source dataset
uspto-grants-1986_06
Patent number
US04595689

Reaction notes

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