Triethylamine → HCID 59750149, compound

HRID 748145Notes

Reaction equation

HRID 748145 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-c1d934e5820b4be3ba17273dfd846025
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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