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

HRID 499300Notes

Reaction equation

HRID 499300 reaction equation
[SH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)#[N:14]>N1C=CC=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[S:1][C:2]=2[CH:10]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 139616424-Methoxy-2-sulfanylbenzoic acid

Product 1

HCID 597501107-methoxy-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-mercapto-4-methoxybenzoic acid (1.4 g, 7.9 mmol), 2-cyanopyridine (0.89 g, 8.5 mmol) and pyridine (10 ml) was refluxed for 10 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 (1.0 g, 47%) as crystals.

Workup

  1. temperaturewas refluxed for 10 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-5eecfc02d78b4f59b45d1416fb6018e4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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