Pyridine-2-carbonitrile → 2-(2-Pyridyl)-7-trifluoromethyl-4H-1,3-benzothiazine-4-one

HRID 499340Notes

Reaction equation

HRID 499340 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([SH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)#[N:16]>N1C=CC=CC=1>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]1[S:12][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:14])[F:13])[CH:11]=[CH:10][C:6]=2[C:7](=[O:9])[N:16]=1

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 215421322-Mercapto-4-(trifluoromethyl)benzoic acid

Product 1

HCID 597503202-(2-Pyridyl)-7-trifluoromethyl-4H-1,3-benzothiazine-4-oneYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-trifluoromethylthiosalicylic acid (2.5 g, 11 mmol), 2-cyanopyridine (1.2 g, 11 mmol) and pyridine (10 ml) was refluxed for 10 hrs. After cooling, the precipitated crystals were collected by filtration and recrystallized from tetrahydrofuran-hexane to give the titled compound (1.9 g, 54%).

Workup

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

Sources & evidence

ORD record
ord-b4113e5a5545491db42edf21d24d59c9
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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