Triethylamine → 2-(4-Cyano-2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499397Notes

Reaction equation

HRID 499397 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]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:20]([C:18]1[CH:17]=[CH:16][N:15]=[C:14]([C:12]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:13]=2)[CH:19]=1)#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 1201442,4-Pyridinedicarbonitrile

Product 1

HCID 597504122-(4-Cyano-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.65 g, 3.9 mmol), 2,4-dicyanopyridine (0.50 g, 3.9 mmol), triethylamine (0.81 ml, 5.8 mmol) and toluene (2.0 ml) was refluxed for 2.5 hrs. After cooling, the precipitated crystals were collected by filtration and recrystallized from acetone-chloroform to give the titled compound (0.54 g, 53%).

Workup

  1. temperaturewas refluxed for 2.5 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from acetone-chloroform

Sources & evidence

ORD record
ord-18b82590e20a4bfe96d0243f401d17bd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…