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

HRID 499263Notes

Reaction equation

HRID 499263 reaction equation
[Br: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>[Br: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 123255215-Bromo-2-mercaptobenzoic acid

Product 1

HCID 597503796-Bromo-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 46.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-mercaptobenzoic acid (4.10 g, 17.6 mmol), 2-cyanopyridine (1.70 g, 16.3 mmol) and pyridine (50.0 ml) were refluxed for 9 hrs as described in Example 9. After cooling, the precipitated crystals were collected and recrystallized from hexane-chlorobenzene to give the titled compound (2.40 g, 45%).

Workup

  1. temperatureAfter cooling
  2. customthe precipitated crystals were collected
  3. customrecrystallized from hexane-chlorobenzene

Sources & evidence

ORD record
ord-e25ee4bc7be44fa19abb7374d78a2a2a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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