Water → HCID 22742446, compound

HRID 2270917Notes

Reaction equation

HRID 2270917 reaction equation
[CH3:1][C:2]1[C:15]2[N:14]([CH2:16][CH2:17][CH2:18]N)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7](=[O:20])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:21].Br[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][C:2]1[C:15]2[N:14]([CH2:16][CH2:17][CH2:18][CH2:23][C:24]#[N:25])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7](=[O:20])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 98611441,2-Dimethyl-10-(3-aminopropyl)phenothiazine-5-oxide

Product 1

HCID 22742446HCID 22742446, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2.25 g of 1,2-dimethyl-10-(3-aminopropyl)phenothiazine-5-oxide synthesized in Example 8, 990 mg of bromoacetonitrile and 1.2 g of potassium carbonate were dissolved in 50 ml of N,N-dimethylformamide followed by stirring at 80° C. for 10 min. Then the reaction mixture was cooled to room temperature and, after adding water, extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give 670 mg of the title compound.

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporating the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-101926e03a8b4ce1a211697a10cf9e5b
Source dataset
uspto-grants-2001_12
Patent number
US06333322B1

Reaction notes

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