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

HRID 499512Notes

Reaction equation

HRID 499512 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Br:9][C:10]1[CH:11]=[C:12]([SH:19])[C:13](=[CH:17][CH:18]=1)[C:14](O)=[O:15]>N1C=CC=CC=1>[Br:9][C:10]1[CH:18]=[CH:17][C:13]2[C:14](=[O:15])[N:2]=[C:1]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)[S:19][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 166561284-Bromo-2-sulfanylbenzoic acid

Product 1

HCID 597503477-Bromo-2-(2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 36.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Cyanopyridine (0.29 g, 2.8 mmol) and 4-bromothiosalicylic acid (0.8 g, 3.4 mmol) were dissolved in pyridine (6 ml), and the mixture was refluxed for 8 hrs. The solvent was evaporated, and the residue was subjected to silica gel column chromatography. The fractions eluted with chloroform-ethyl acetate (5:1, v/v) were collected, concentrated and recrystallized from hexane-chloroform to give the titled compound (0.33 g, 36%) as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 8 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with chloroform-ethyl acetate (5:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-e71d66cfa01a4d49b14516b5f91c4cd3
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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