Triethylamine → HCID 59750196, compound

HRID 499341Notes

Reaction equation

HRID 499341 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-07b0ee3d9f6a44f5af6a6e95b0f583a4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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