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

HRID 748099Notes

Reaction equation

HRID 748099 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-dfcccadbec9f4f7f9eeb0b9d2fca53b0
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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