Water → 12-Acetyl-5-methoxy-12H-benzo[a]phenothiazine

HRID 64963Notes

Reaction equation

HRID 64963 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([N:10]1[C:23]2[C:18](=[CH:19][C:20]([OH:28])=[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]3=2)[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:9])[CH3:8].CI.O>CN(C=O)C>[C:7]([N:10]1[C:23]2[C:18](=[CH:19][C:20]([O:28][CH3:1])=[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]3=2)[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 1371248512-acetyl-5-hydroxy-12H-benzo[a]phenothiazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 1371248612-Acetyl-5-methoxy-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (800 mg) was added to a solution of 12-acetyl-5-hydroxy-12H-benzo[a]phenothiazine (950 mg) (from Example 3) and methyl iodide (1.5 ml) in DMF (10 ml) and stirred for 15 minutes. Water (80 ml) was added to the reaction mixture and the precipitate was filtered to afford the title compound.

Workup

  1. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-b694f4419f0c49708dc08209ccec080e
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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