Triethylamine → HCID 59750130, compound

HRID 499317Notes

Reaction equation

HRID 499317 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH2:12]([N:19]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][N:28]=1)[C:24]#[N:25])[CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([N:19]([C:21]1[CH:22]=[C:23]([C:24]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:25]=2)[CH:26]=[CH:27][N:28]=1)[CH3:20])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 246948332-[Benzyl(methyl)amino]pyridine-4-carbonitrile

Product 1

HCID 59750130HCID 59750130, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (0.70 g, 4.2 mmol) and 2-[N-benzyl-N-methylamino]isonicotinonitrile (0.46 g, 2.1 mmol) were dissolved in toluene (2.0 ml), and triethylamine (0.68 ml, 4.9 mmol) was added thereto. The reaction mixture was refluxed for 8 hrs, subjected to silica gel (50 g) column chromatography, eluted with hexane-ethyl-acetate (2:1, v/v) and recrystallized from ethanol to give the titled compound (0.23 g, 15%).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hrs
  2. washeluted with hexane-ethyl-acetate (2:1
  3. customv/v) and recrystallized from ethanol

Sources & evidence

ORD record
ord-4bda2a57b283453dab4983793dafe3fd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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