Triethylamine → HCID 59750196, compound

HRID 748159Notes

Reaction equation

HRID 748159 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=1)[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15]1[N:16]=[CH:17][C:18]([C:21]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:22]=2)=[CH:19][CH:20]=1)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 189294456-Ethoxypyridine-3-carbonitrile

Product 1

HCID 59750196HCID 59750196, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.85 g, 11.0 mmol), 2-ethoxy-5-cyanopyridine (1.48 g, 10.0 mmol), triethylamine (1.80 ml, 12.9 mmol) and toluene (10 ml) was refluxed under nitrogen atmosphere for 18 hrs. The reaction mixture was concentrated. The residue was combined with water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (2:1, v/v) and recrystallized from chloroform-ethyl acetate to give the titled compound (0.56 g, 20%).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 18 hrs
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. washeluted with ethyl acetate-hexane (2:1
  8. customv/v) and recrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-eda37638ba8d4199b0b5251f38af43ed
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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