Triethylamine → HCID 59750336, compound

HRID 499382Notes

Reaction equation

HRID 499382 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:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:16]1[N:15]=[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:19]=[CH:18][CH:17]=1)[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 13023645HCID 13023645, compound

Product 1

HCID 59750336HCID 59750336, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.17 g, 1.0 mmol), 2-cyano-6-ethoxypyridine (0.15 g, 1.0 mmol), triethylamine (0.21 ml, 1.5 mmol) and toluene (30 ml) was refluxed for 48 hrs. The reaction mixture was concentrated under reduced pressure. The residue was subjected to a column chromatography and eluted with hexane-ethyl acetate (3:1, v/v). The obtained crystals were recrystallized from ethyl acetate-hexane to give the titled compound (0.04 g, 14%).

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (3:1
  4. customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-80532c15be6b415bb0e5658eae64e3fb
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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