Diethyl Ether → 5-methoxy-12-methyl-12H-benzo[a]phenothiazine

HRID 64961Notes

Reaction equation

HRID 64961 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([O:10][C:11]1[CH:24]=[C:23]2[C:14]([NH:15][C:16]3[C:21]([S:22]2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:13]2[CH:25]=[CH:26][CH:27]=[CH:28][C:12]=12)(=O)C.CI.C(OCC)C>CN(C=O)C.[Cl-].[Na+].O>[CH3:7][O:10][C:11]1[CH:24]=[C:23]2[C:14]([N:15]([CH3:1])[C:16]3[C:21]([S:22]2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:13]2[CH:25]=[CH:26][CH:27]=[CH:28][C:12]=12

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 137124795-acetoxy-12H-benzo[a]phenothiazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 137124835-methoxy-12-methyl-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium tert. butoxide (1.3 gm) was added to a solution of 5-acetoxy-12H-benzo[a]phenothiazine (from Example 1) (2.0 gm) and methyl iodide (4 ml) in DMF (20 ml). The reaction mixture was cooled with an ice-bath and stirred for 15 minutes. Diethyl ether (100 ml) was added to the reaction mixture followed by brine (100 ml). The ether layer was decanted, washed with brine, dried and evaporated to dryness. The resulting oily residue was chromatographed on silica gel (10% EtOAc/hexane) to afford 5-methoxy-12-methyl-12H-benzo[a]phenothiazine.

Workup

  1. temperatureThe reaction mixture was cooled with an ice-bath
  2. customThe ether layer was decanted
  3. washwashed with brine
  4. customdried
  5. customevaporated to dryness
  6. customThe resulting oily residue was chromatographed on silica gel (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-24eef094ff484bfca05ec2cb6d8ee2a1
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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