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

HRID 748227Notes

Reaction equation

HRID 748227 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OC)(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[SH:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([S:8][C:9]1[N:10]=[C:11]([C:15]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17](=[O:25])[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229396226-(Benzylthio)picolinonitrile

Product 1

HCID 229395932-(6-Benzylthio-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Benzylthio-6-cyanopyridine (1.63 g, 7.22 mmol) and methyl thiosalicylate (1.21 g, 7.22 mmol) were dissolved in toluene (30 ml), and triethylamine (1.52 ml, 10.8 mmol) was added thereto. The reaction mixture was refluxed for 48 hrs. The solvent was evaporated and the residue was recrystallized from ethanol to give the titled compound (1.03 g, 44%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. customThe solvent was evaporated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a7c6ab6062824890aa342d84b6044cc4
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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