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

HRID 499295Notes

Reaction equation

HRID 499295 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-c22c970a9d16459db2bb457ea462f095
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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