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

HRID 499362
Notes
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Reaction equation

HRID 499362 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][OH:23].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[OH:23][CH2:22][CH2:21][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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 229394706-hydroxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

Product 1

HCID 597503506-(3-Hydroxypropoxy)-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 57.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 6-hydroxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one (0.40 g, 1.5 mmol), 3-bromo-1-propanol (0.66 g, 4.7 mmol) and potassium carbonate (0.43 g, 3.1 mmol) and DMF (10 ml) was stirred at room temperature for 15 hrs. The reaction mixture was diluted with water and extracted with a mixture solvent of ethyl acetate and ethanol. The extract was washed with water and dried. The solvent was evaporated. The obtained crystals were recrystallized from ethanol-hexane to give the titled compound (0.27 g, 54%).

Workup

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

Sources & evidence

ORD record
ord-dc5d24420dcc44edb323ab755716855e
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes