Methyl iodide → 1-(10-Methyl-10H-phenothiazin-2-yl)ethan-1-one

HRID 1087391Notes

Reaction equation

HRID 1087391 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[CH3:18]C(C)([O-])C.[K+].CI.C(OCC)(=O)C>CN(C)C=O>[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH3:18])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 81131Methyl phenothiazin-2-yl ketoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 914011-(10-Methyl-10H-phenothiazin-2-yl)ethan-1-oneYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-acetylphenothiazine (Aldrich) (2.41 g, 10 mmol) in dimethylformamide (25 mL) was added potassium t-butoxide (1.5 g, 13.4 mmol) and the mixture was stirred for 15 minutes. Methyl iodide (1.9 g, 13.4 mmol) was then added, dropwise, to the resulting solution and the mixture stirred for 30 minutes. Ice-water was added to the reaction mixture followed by ethyl acetate. The organic layer was decanted, washed with brine, dried over Na2SO4 and evaporated to dryness. The oily residue was chromatographed on flash silica gel eluting with 10% ethyl acetate/hexane to afford the pure title product (1.0 g, 39%).

Workup

  1. stirringdropwise, to the resulting solution and the mixture stirred for 30 minutes
  2. customThe organic layer was decanted
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe oily residue was chromatographed on flash silica gel eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-cfe2820686dd4c8d8b3bc5abd3bb9545
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Reaction notes

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