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

HRID 499386

Reaction equation

HRID 499386 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]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:20]1([C:18]2[CH:17]=[CH:16][N:15]=[C:14]([C:12]3[S:4][C:3]4[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=4[C:1](=[O:10])[N:13]=3)[CH:19]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 877584-Phenyl-2-pyridinecarbonitrile

Product 1

HCID 597501042-(4-Phenyl-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.00 g, 5.9 mmol), 2-cyano-4-phenylpyridine (1.10 g, 5.9 mmol), triethylamine (1.30 ml, 9.0 mmol) and toluene (2.5 ml) was refluxed for 20 hrs. After cooling, the precipitated crystals were collected by filtration and recrystallized from ethanol to give the titled compound (0.99 g, 53%).

Workup

  1. temperaturewas refluxed for 20 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-91eb6428f2b94a009d6e64f5151a335e
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Linked notes

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