Phenothiazine → Methyl phenothiazin-10-yl ketone

HRID 1686372Notes

Reaction equation

HRID 1686372 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C1(C)C(C)=CC=CC=1>[C:15]([N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7108PhenothiazineHCID 7918Acetic Anhydride

Product 1

HCID 74200Methyl phenothiazin-10-yl ketoneYield 93.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The 10-acetylphenothiazine of formula (5) was synthesized by the following method. A 200-ml four-neck flask was loaded with 19.93 g (0.1 mole) of phenothiazine, 15.31 g (0.15 mole) of acetic anhydride, and 40 g of xylene, and the contents were subjected to heating under reflux conditions for 6 hours. The reaction liquid was cooled, the precipitate was separated by filtering, and the product washed with methanol. As a result, 22.6 g of 10-acetylphenothiazine having a molecular weight of 241.3 were obtained.

Workup

  1. temperatureto heating under reflux conditions for 6 hours
  2. customThe reaction liquid
  3. temperaturewas cooled
  4. customthe precipitate was separated
  5. filtrationby filtering
  6. washthe product washed with methanol

Sources & evidence

ORD record
ord-9129b051359149dcb01e9ff95a9eabdc
Source dataset
uspto-grants-2012_04
Patent number
US08148565B2

Reaction notes

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