Pyridine-2-carbonitrile → 5-Methyl-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 748091Notes

Reaction equation

HRID 748091 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([SH:11])[CH:5]=[CH:4][CH:3]=1.[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:7]2[C:8](=[O:10])[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[S:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 126128092-Mercapto-6-methylbenzoic acid

Product 1

HCID 597501765-Methyl-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 20%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 6-methyl-2-mercaptobenzoic acid (1.70 g, 10.1 mmol), 2-cyanopyridine (1.06 g, 10.2 mmol) and pyridine (30.0 ml) was refluxed at 135° C. for 18 hrs as described in Example 9. The reaction mixture was concentrated. The residue was subjected to a silica gel column chromatography and eluted with ethyl acetate. The resultant product was recrystallized from ethanol to give the titled compound (0.51 g, 20%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washeluted with ethyl acetate
  3. customThe resultant product was recrystallized from ethanol

Sources & evidence

ORD record
ord-96ee66f7ee924d06b1e9cac227ebe0ab
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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