Methanol → 4-chloro-3-methoxy-10-acetyl-10H-phenothiazine

HRID 231045Notes

Reaction equation

HRID 231045 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([S:16][C:17]=2[C:18]=1[Cl:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)(=O)C.[CH3:20]I.[H-].[Na+].CO.CN([CH:29]=[O:30])C>O>[Cl:19][C:18]1[C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:29](=[O:30])[CH3:20])[C:8]=2[CH:7]=[CH:6][C:5]=1[O:4][CH3:1]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 138820263-acetoxy-4-chloro-10H-phenothiazine

Product 1

HCID 138820284-chloro-3-methoxy-10-acetyl-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-chloro-3-acetoxy-10H-phenothiazine (see Example 4) in DMF (10 mls) was added methyl iodide (0.34 ml) and sodium hydride (114 mg). The reaction mixture was stirred at ambient temperature for 12 hours. Methanol and water were then added and the resulting mixture extracted with EtOAc. The organic phases were then collected, dried and evaporated. The resulting residue was purified by chromatography on silica gel (HPLC) to give 0.56 g of 4-chloro-3-methoxy-10-acetyl-10H-phenothiazine (m.p. 136° C.).

Workup

  1. extractionthe resulting mixture extracted with EtOAc
  2. customThe organic phases were then collected
  3. customdried
  4. customevaporated
  5. customThe resulting residue was purified by chromatography on silica gel (HPLC)

Sources & evidence

ORD record
ord-8338ac6bd3384ca9b827e7ce62c569d7
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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