Triethylamine → tert-Butyl (E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoate

HRID 499403Notes

Reaction equation

HRID 499403 reaction equation
[C:1]([C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:18](OC)(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[SH:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:26]=[C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:1]([C:3]2[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 70859748tert-Butyl (E)-3-(6-cyano-2-pyridyl)-2-propenoate

Product 1

HCID 59750467tert-Butyl (E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoateYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (E)-3-(6-cyano-2-pyridyl)-2-propenoate (2.32 g, 10.1 mmol) and methyl thiosalicylate (1.86 g, 11.0 mmol) were dissolved in toluene (12 ml), and triethylamine (1.63 g, 25.7 mmol) was added thereto. The reaction mixture was refluxed for 38 hrs, concentrated, subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (5:2, v/v) to give the titled compound (0.78 g, 27%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 38 hrs
  2. concentrationconcentrated
  3. washeluted with hexane-ethyl acetate (5:2

Sources & evidence

ORD record
ord-9570793c6e434d29bcf68cfd27e95252
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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