Triethylamine → HCID 59750374, compound

HRID 748140Notes

Reaction equation

HRID 748140 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[N:12]1([C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][N:25]=2)[C:21]#[N:22])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:12]1([C:18]2[CH:19]=[C:20]([C:21]3[S:4][C:3]4[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=4[C:1](=[O:10])[N:22]=3)[CH:23]=[CH:24][N:25]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 146408562-(Morpholin-4-yl)pyridine-4-carbonitrile

Product 1

HCID 59750374HCID 59750374, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (0.49 g, 2.9 mmol) and 2-morpholinylisonicotinonitrile (0.38 g, 2.0 mmol) were dissolved in toluene (2.0 ml), and triethylamine (0.48 ml, 3.4 mmol) was added thereto. The reaction mixture was refluxed for 14 hrs. After cooling, the precipitated crystals were collected by filtration and recrystallized from ethanol. The obtained crystals were recrystallized from ethyl acetate again to give the titled compound (0.16 g, 25%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 14 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from ethanol
  5. customThe obtained crystals were recrystallized from ethyl acetate again

Sources & evidence

ORD record
ord-cc82206267b54091ae3a766ea1bd1a3a
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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