Diethyl Ether → 4-Diethoxymethyl-10-methyl-phenothiazine

HRID 2395161Notes

Reaction equation

HRID 2395161 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.[CH3:11][N:12]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21](C=O)[C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2.C(=O)([O-])O.[Na+].C(OCC)C>CO>[CH2:9]([O:8][CH:1]([O:5][CH2:6][CH3:7])[C:21]1[C:20]2[S:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH3:11])[C:25]=2[CH:24]=[CH:23][CH:22]=1)[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 3812154HCID 3812154, compound

Product 1

HCID 189725154-Diethoxymethyl-10-methyl-phenothiazineYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.0 ml of triethyl orthoformate were added at room temperature to a solution of 4.90 g (20.3 mmol) of 10-methyl-phenothiazine-4-carbaldehyde and 50 mg of p-toluenesulphonic aci×1H2O in 15 ml of methanol. The reaction mixture was boiled at reflux for 45 minutes, cooled and poured into 30 g of ice, 30 ml of saturated aqueous sodium hydrogen carbonate solution and 100 ml of diethyl ether. The organic phase was washed with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on 300 g of silica gel with diethyl ether/hexane (1:4), whereupon, after crystallization from diethyl ether/hexane in a refrigerator, 6.16 g (96.2%) of 4-diethoxymethyl-10-methyl-phenothiazine were obtained as a white solid of m.p. 44.6°-46.2°.

Workup

  1. temperatureat reflux for 45 minutes
  2. temperaturecooled
  3. washThe organic phase was washed with 50 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on 300 g of silica gel with diethyl ether/hexane (1:4), whereupon
  7. customafter crystallization from diethyl ether/hexane in a refrigerator

Sources & evidence

ORD record
ord-1dd7eebba0b94059bb2fc44ff392bb7e
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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