Triethylamine → 2-[5-(trifluoromethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one

HRID 748117Notes

Reaction equation

HRID 748117 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][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:22][C:20]([F:21])([F:23])[C:17]1[CH:18]=[CH:19][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)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 15353725-(Trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 597500952-[5-(trifluoromethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.43 g, 2.6 mmol), 2-cyano-5-trifluoromethylpyridine (0.44 g, 2.6 mmol), triethylamine (0.60 ml, 3.8 mmol) and toluene (30 ml) was refluxed for 48 hrs as described in Example 1. The solvent was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the titled compound (0.18 g, 23%) as crystals.

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-39c597c224a14c209a14db298071cfd7
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…