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Propyl mercaptan → 2-[6-[(n-Propylthio)methyl]-2-pyridyl]-4H-1,3-benzothiazine-4-one

HRID 499523
Notes
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Reaction equation

HRID 499523 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].[H-].[Na+].CS(O[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[S:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22](=[O:24])[N:23]=2)[N:13]=1)(=O)=O.[C:29](OCC)(=O)C>CN(C=O)C.O>[CH2:1]([S:4][CH2:29][C:12]1[N:13]=[C:14]([C:18]2[S:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22](=[O:24])[N:23]=2)[CH:15]=[CH:16][CH:17]=1)[CH2:2][CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7848Propyl mercaptanHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate

Product 1

HCID 597504462-[6-[(n-Propylthio)methyl]-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 20%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

n-Propyl mercaptan (0.25 g, 3.30 mmol) and sodium hydride (60% in oil, 0.15 g, 3.60 mmol) were dissolved in DMF (30 ml), and 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate (1.05 g, 3.00 mmol) was added thereto. The reaction mixture was stirred at room temperature for 18 hrs, combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from n-hexane-ethyl acetate to give the titled compound (0.20 g, 20%) as pale yellow crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-f8b491ac082f4fe191c955cae97ca7d6
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