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

HRID 1920616Notes

Reaction equation

HRID 1920616 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 triethylamine (2 ml, 14.4 mM) was added to the solution. After heating for 8 hours under reflux, toluene was removed by distillation. Ethanol was added to the residue and the precipitates were taken out by filtration to give crude crystals (1.7 g). The crude crystals were 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 for 8 hours
  2. temperatureunder reflux
  3. customtoluene was removed by distillation
  4. additionEthanol was added to the residue
  5. filtrationthe precipitates were taken out by filtration
  6. customto give crude crystals (1.7 g)
  7. customThe crude crystals were purified by silica gel column chromatography (hexane:chloroform=5:1→chloroform)

Sources & evidence

ORD record
ord-0ca57061b15746d2a4663153f923d3b2
Source dataset
uspto-grants-2012_05
Patent number
US08173360B2

Reaction notes

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