Triethylamine → HCID 59750449, compound

HRID 499344Notes

Reaction equation

HRID 499344 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]=[CH:16][C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])=[N:18][CH:19]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:24]([O:23][CH2:22][CH2:21][O:20][C:17]1[N:18]=[CH:19][C:14]([C:12]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:13]=2)=[CH:15][CH:16]=1)[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939609HCID 22939609, compound

Product 1

HCID 59750449HCID 59750449, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.96 g, 17.6 mmol), 5-cyano-2-(2-ethoxy)ethoxypyridine (3.07 g, 16.0 mmol), triethylamine (2.37 ml, 17.0 mmol) and toluene (15 ml) was refluxed under nitrogen atmosphere for 40 hrs. The reaction mixture was concentrated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (1:1, v/v) and recrystallized from acetone-ethyl acetate-isopropylether to give the titled compound (3.01 g, 57%).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 40 hrs
  2. concentrationThe reaction mixture was concentrated
  3. washeluted with ethyl acetate-hexane (1:1
  4. customv/v) and recrystallized from acetone-ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-f04f2ce6846f4650a03b3dd7fdaba562
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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