Triethylamine → 2-(6-Methoxy-2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499302Notes

Reaction equation

HRID 499302 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]=[C:16]([O:20][CH3:21])[N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:21][O:20][C:16]1[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]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 130236446-Methoxy-2-pyridinecarbonitrile

Product 1

HCID 597503942-(6-Methoxy-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 13.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.56 g, 3.4 mmol), 2-cyano-6-methoxypyridine (0.45 g, 3.4 mmol), triethylamine (0.70 ml, 5.0 mmol) and toluene (50 ml) was refluxed for 48 hrs as described in Example 1. The reaction mixture was concentrated under reduced pressure and recrystallized from ethanol to give the titled compound (0.12 g, 13%) as crystals.

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dadddd4669fd43e4b4f49bdaca3d5991
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…