Pyridine-2-carbonitrile → 8-Methyl-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499264Notes

Reaction equation

HRID 499264 reaction equation
[CH3:1][C:2]1[C:3]([SH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)#[N:13]>N1C=CC=CC=1>[CH3:1][C:2]1[C:3]2[S:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:13][C:5](=[O:7])[C:4]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 126128083-Methyl-2-sulfanylbenzoic acid

Product 1

HCID 597501058-Methyl-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 52.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-methyl-2-mercaptobenzoic acid (2.40 g, 14.3 mmol), 2-cyanopyridine (1.20 g, 11.9 mmol) and pyridine (50.0 ml) was refluxed for 9 hrs as described in Example 9. After cooling, the precipitated crystals were collected by filtration and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.60 g, 52%)

Workup

  1. temperaturewas refluxed for 9 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-cb2778578d9045b195dee83e9288573c
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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