Triethylamine → tert-Butyl 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylate

HRID 499336Notes

Reaction equation

HRID 499336 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].[C:16](OC)(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[SH:19].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:24]=[C:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[S:19][C:1]([C:3]2[N:8]=[C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939377tert-Butyl 6-cyanopicolinate

Product 1

HCID 22939348tert-Butyl 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylateYield 72.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl 6-cyano-2-pyridinecarboxylate (1.1 g, 5.3 mmol), methyl thiosalicylate (1.8 g, 10.7 mmol), triethylamine (2.0 ml, 14.3 mmol) and toluene (4 ml) was refluxed for 12 hrs. After cooling, the precipitated crystals were collected by filtration, recrystallized from tetrahydrofuran-hexane to give the titled compound (1.3 g, 70%).

Workup

  1. temperaturewas refluxed for 12 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-bb5cce6883534532bcb433876ff56e9b
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…