Triethylamine → HCID 22939578, compound

HRID 748146Notes

Reaction equation

HRID 748146 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[C:17]([C:19]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:20]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 22939578HCID 22939578, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (3.6 g, 21.6 mmol) and 2-chloro-4-cyanopyridine (3.0 g, 21.7 mmol) were dissolved in toluene (5.0 ml), and triethylamine (4.5 ml, 32.3 mmol) was added thereto. The reaction mixture was refluxed for 22 hrs. The reaction mixture was subjected to a silica gel (120 g) column chromatography, eluted with hexane-ethyl acetate (1:2, v/v) and recrystallized from acetone-ethyl acetate to give 2-(2-chloro-4-pyridyl)-4H-1,3-benzothiazine-4-one (0.47 g, 8.0%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 22 hrs
  2. washeluted with hexane-ethyl acetate (1:2
  3. customv/v) and recrystallized from acetone-ethyl acetate

Sources & evidence

ORD record
ord-a7b28bdc1c724f5c824dbbaeeff3d2c3
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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