3-Methyl-2-sulfanylbenzoic acid → tert-Butyl 6-(8-methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylate

HRID 499501Notes

Reaction equation

HRID 499501 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=1)#[N:2].[CH3:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:19]([C:20](O)=[O:21])[C:18]=1[SH:26]>N1C=CC=CC=1>[CH3:16][C:17]1[C:18]2[S:26][C:1]([C:3]3[N:8]=[C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=3)=[N:2][C:20](=[O:21])[C:19]=2[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 126128083-Methyl-2-sulfanylbenzoic acidHCID 22939377tert-Butyl 6-cyanopicolinate

Product 1

HCID 22939413tert-Butyl 6-(8-methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylateYield 58.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl 6-cyano-2-pyridinecarboxylate (3.2 g, 15 mmol) and 3-methylthiosalicylic acid (4.7 g, 28 mmol) were dissolved in pyridine (40 ml), and the mixture was refluxed for 16 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-tetrahydrofuran (2:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (3.1 g, 56%) as pale yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 16 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-tetrahydrofuran (2:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-b052ffc30c134d6aa4a02440c773f99c
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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