Triethylamine → HCID 59750154, compound

HRID 748101Notes

Reaction equation

HRID 748101 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:15]=[C:16]([CH:22]=[CH:23][N:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[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:15]=[C:16]([CH:22]=[CH:23][N:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 13415157Ethyl 2-cyanopyridine-4-carboxylate

Product 1

HCID 59750154HCID 59750154, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (3.0 g, 17.8 mmol), ethyl 2-cyanoisonicotinate (3.1 g, 17.8 mmol), triethylamine (5.0 ml, 35.8 mmol) and toluene (10 ml) was refluxed for 8 hrs as described in Example 1. The precipitated crystals were collected by filtration and recrystallized from diisopropylether-chlorobenzene to give the titled compound (4.0 g, 71%).

Workup

  1. temperaturewas refluxed for 8 hrs
  2. filtrationThe precipitated crystals were collected by filtration
  3. customrecrystallized from diisopropylether-chlorobenzene

Sources & evidence

ORD record
ord-b42f566ad74c44ada48dd8ef60fde250
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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