Pyridine-2-carbonitrile → 2-(2-pyridyl)-4H-1,3-benzothiazin-4-one

HRID 1007126Notes

Reaction equation

HRID 1007126 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]1[S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1](=[O:10])[N:13]=1

Participants

5

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl ester

Product 1

HCID 98376402-(2-pyridyl)-4H-1,3-benzothiazin-4-oneYield 43.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (1.6 g, 9.51 mM) and 2-cyanopyridine (1.0 g, 9.60 mM) were dissolved in toluene (2 ml), and then triethylamine (2 ml, 14.4 mM) was added thereto. After heating the mixture under reflux for 8 hours, and the toluene was distilled away. Ethanol was added to the residues, and the resulting precipitates were collected by filtration to give crude crystals (1.7 g). The product was purified by silica gel column chromatography (hexane:chloroform=5:1→chloroform) to give the title compound as crystals (1.0 g, 43.4%).

Workup

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 8 hours
  3. distillationthe toluene was distilled away
  4. additionEthanol was added to the residues
  5. customthe resulting precipitates
  6. filtrationwere collected by filtration
  7. customto give crude crystals (1.7 g)
  8. customThe product was purified by silica gel column chromatography (hexane:chloroform=5:1→chloroform)

Sources & evidence

ORD record
ord-c5f2a9cc35af42238539c94d8797b46b
Source dataset
uspto-grants-2004_09
Patent number
US06794383B2

Reaction notes

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