Water → 1,2-Dimethyl-10-(3-chloropropyl)phenothiazine

HRID 48185Notes

Reaction equation

HRID 48185 reaction equation
[CH3:1][C:2]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:16].[H-].[Na+].[Cl:19][CH2:20][CH2:21][CH2:22]I.O>CN(C=O)C>[CH3:1][C:2]1[C:15]2[N:14]([CH2:22][CH2:21][CH2:20][Cl:19])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 227424451,2-Dimethylphenothiazine

Product 1

HCID 227424361,2-Dimethyl-10-(3-chloropropyl)phenothiazineYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g of 1,2-dimethylphenothiazine in N,N′-dimethylformamide was added 970 mg of sodium hydride under stirring at room temperature. After stirring at room temperature for 30 min, 4.0 g of 1-chloro-3-iodopropane was added dropwise followed by stirring at room temperature overnight. After adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give 3.4 g of the title compound.

Workup

  1. stirringAfter stirring at room temperature for 30 min
  2. stirringby stirring at room temperature overnight
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-983d13628ac74d859a09faafa7a4c6fa
Source dataset
uspto-grants-2004_03
Patent number
US06703388B2

Reaction notes

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