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

HRID 748177Notes

Reaction equation

HRID 748177 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][CH3:23].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:20]([O: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)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 229394706-hydroxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

Product 1

HCID 597503066-Butoxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 86.2%

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-bromobutane (0.38 g, 2.7 mmol) and potassium carbonate (0.56 g, 4.0 mmol) and DMF (10 ml) was stirred at room temperature for 15 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. The obtained crystals were recrystallized from tetrahydrofuran-hexane to give the titled compound (0.35 g, 83%).

Workup

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

Sources & evidence

ORD record
ord-4b9d9f4392fc47d294cbb84a934c9047
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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