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

HRID 499360Notes

Reaction equation

HRID 499360 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-3f41a944faba4bd4a08b0816a1a13da1
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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