Triethylamine → HCID 59750455, compound

HRID 748100Notes

Reaction equation

HRID 748100 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-09e3977e93a84453a2128a31eb78934a
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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