Triethylamine → HCID 59750455, compound

HRID 499278Notes

Reaction equation

HRID 499278 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:12]([C:14]1[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:10]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][C:12]([C:14]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=2)=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 13415158Ethyl 6-cyanopyridine-2-carboxylate

Product 1

HCID 59750455HCID 59750455, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.0 g, 11.9 mmol), ethyl 6-cyano-2-pyridinecarboxylate (2.1 g, 11.9 mmol), triethylamine (3.0 ml, 21.5 mmol) and toluene (6 ml) was refluxed for 12 hrs as described in Example 1. The precipitated crystals were collected by filtration and recrystallized from diisopropylether-tetrahydrofuran to give the titled compound (3.0 g, 80%).

Workup

  1. temperaturewas refluxed for 12 hrs
  2. filtrationThe precipitated crystals were collected by filtration
  3. customrecrystallized from diisopropylether-tetrahydrofuran

Sources & evidence

ORD record
ord-0437013843e14f65891c9c5c5c35af8d
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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