Methyl iodide → HCID 15168927, compound

HRID 1898866Notes

Reaction equation

HRID 1898866 reaction equation
[CH3:1][O-].[K+].[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[O:16][C:15]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:14]=3[NH:13][C:12](=[O:22])[C:11]=2[CH:23]=1)([O-:6])=[O:5].IC>C(O)(C)(C)C.O1CCOCC1>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[O:16][C:15]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:14]=3[N:13]([CH3:1])[C:12](=[O:22])[C:11]=2[CH:23]=1)([O-:6])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 3727890HCID 3727890, compoundHCID 23664618Potassium methoxide

Product 1

HCID 15168927HCID 15168927, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a warm solution of 4.05 g potassium methoxide in 80 ml of t-butanol and 80 ml of dioxane was added 13.5 g (0.05 mol) of 2-nitro-7-methyldibenz[b,f][1,4]oxazepin-11(10H)-one. The resulting suspension was warmed to 60° C. for 15 minutes. Initially everthing went in solution, after several minutes a crystalline precipitate formed. To the stirred suspension was added 3.75 ml of iodomethane. The reaction mixture was stirred for 4 hours at 60° C., then concentrated to dryness in vacuo. The dark residue was suspended in water, acidified with acetic acid, concentrated in vacuo and then recrystallized from propanol to give 8.5 g (60% yield) of 2-nitro-7,10-dimethyldibenz[b,f][1,4]- oxazepin-11(10H)-one mp 156°-159°.

Workup

  1. waitInitially everthing went in solution, after several minutes
  2. customa crystalline precipitate formed
  3. concentrationconcentrated to dryness in vacuo
  4. concentrationconcentrated in vacuo
  5. customrecrystallized from propanol

Sources & evidence

ORD record
ord-c55c40208e0445ec8ff26ba8c93a35f2
Source dataset
uspto-grants-1996_11
Patent number
US05571806

Reaction notes

Loading…