Triethylamine → HCID 59750474, compound

HRID 499280Notes

Reaction equation

HRID 499280 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[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N: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[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N:15]=2)=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 13144281Methyl 6-cyanopyridine-3-carboxylate

Product 1

HCID 59750474HCID 59750474, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.1 g, 12.3 mmol), methyl 6-cyanonicotinate (2.0 g, 12.3 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-chlorobenzene to give the titled compound (2.1 g, 58%).

Workup

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

Sources & evidence

ORD record
ord-0b716a455cb3434eb2ff91075412c8ae
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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