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

HRID 499277Notes

Reaction equation

HRID 499277 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:21]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 134151564-Methoxypyridine-2-carbonitrile

Product 1

HCID 597503902-(4-Methoxy-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.0 g, 11.7 mmol), 4-methoxy-2-cyanopyridine (1.5 g, 11.1 mmol), triethylamine (2.5 ml, 17.9 mmol) and toluene (5 ml) was refluxed for 12 hrs as described in Example 1. The precipitated crystals were collected by filtration and recrystallized from hexane-chlorobenzene to give the titled compound (2.4 g, 81%)

Workup

  1. temperaturewas refluxed for 12 hrs
  2. filtrationThe precipitated crystals were collected by filtration
  3. customrecrystallized from hexane-chlorobenzene

Sources & evidence

ORD record
ord-a17444bbbcda4c6d9410bb99e8b87064
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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