Triethylamine → HCID 59750149, compound

HRID 499326Notes

Reaction equation

HRID 499326 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1C=[N:23][CH:22]=[CH:21][C:18]=1C#N.[CH2:25]([N:27](CC)CC)[CH3:26]>C1(C)C=CC=CC=1>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[CH:18]=[C:21]([C:22]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:23]=2)[CH:26]=[CH:25][N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 68454252HCID 68454252, compound

Product 1

HCID 59750149HCID 59750149, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (0.38 g, 2.2 mmol) and (2-thienyl)isonicotinonitrile (0.26 g, 1.4 mmol) were dissolved in toluene (2.0 ml), and triethylamine (0.39 ml, 2.8 mmol) was added thereto. The reaction mixture was refluxed for 24 hrs. The reaction mixture was subjected to a silica gel (30 g) column chromatography, eluted with hexane-ethyl acetate (2:1, v/v) and recrystallized from ethanol to give the titled compound (0.22 g, 30%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hrs
  2. washeluted with hexane-ethyl acetate (2:1
  3. customv/v) and recrystallized from ethanol

Sources & evidence

ORD record
ord-fdd698aa1e8b4753b640f0c8393036fd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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