Dimethylformamide → 6-(3-Phenylpropoxy)-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 748181Notes

Reaction equation

HRID 748181 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:8][C:7](=[O:17])[C:6]=2[CH:18]=1.Br[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:23]1([CH2:22][CH2:21][CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5]3[S:10][C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[N:8][C:7](=[O:17])[C:6]=3[CH:18]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 229394706-hydroxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

Product 1

HCID 597501196-(3-Phenylpropoxy)-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-hydroxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one (0.35 g, 1.3 mmol), 1-bromo-3-phenylpropane (0.86 g, 4.3 mmol) and potassium carbonate (0.38 g, 2.7 mmol) and DMF (10 ml) was stirred at room temperature for 20 hrs. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from tetrahydrofuran-hexane to give the titled compound (0.48 g, 92%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained crystals were recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-161fcb4c802a483fbacd280926265feb
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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