Pyridine-2-carbonitrile → 6-Fluoro-2-(2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499272Notes

Reaction equation

HRID 499272 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([SH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)#[N:13]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:13][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 27833715-Fluoro-2-mercaptobenzoic acid

Product 1

HCID 597504776-Fluoro-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 5-fluoro-2-mercaptobenzoic acid (1.50 g, 8.7 mmol), 2-cyanopyridine (0.92 g, 8.8 mmol) and pyridine (30.0 ml) was refluxed at 135° C. for 48 hrs as described in Example 9. The reaction mixture was concentrated. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v). The resultant product was recrystallized from ethanol to give the titled compound (0.09 g, 4%).

Workup

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

Sources & evidence

ORD record
ord-887478f8a4ea48acbb100b857cb5eafb
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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