Pyridine-2-carbonitrile → 7-Methyl-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499285Notes

Reaction equation

HRID 499285 reaction equation
[SH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)#[N:13]>N1C=CC=CC=1>[CH3:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[S:1][C:2]=2[CH:10]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 200954184-Methyl-2-sulfanylbenzoic acid

Product 1

HCID 597501577-Methyl-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-mercapto-4-methylbenzoic acid (2.0 g, 12 mmol), 2-cyanopyridine (1.4 g, 13 mmol) and pyridine (8 ml) was refluxed for 14 hrs as described in Example 9. After cooling, the precipitated crystals were collected by filtration, subjected to a silica gel column chromatography, eluted with ethyl acetate-methanol (5:1, v/v) and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.4 g, 48%).

Workup

  1. temperaturewas refluxed for 14 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washeluted with ethyl acetate-methanol (5:1
  5. customv/v) and recrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-6dcc5e3820db4c488a5522bdd1a1a88a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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