Triethylamine → HCID 59750346, compound

HRID 499343Notes

Reaction equation

HRID 499343 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][N:17]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:12]([O:15][C:16]1[N:17]=[CH:18][C:19]([C:22]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:23]=2)=[CH:20][CH:21]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229393206-[(Propan-2-yl)oxy]pyridine-3-carbonitrile

Product 1

HCID 59750346HCID 59750346, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.85 g, 11.0 mmol), 2-isopropoxy-5-cyanopyridine (1.62 g, 10.0 mmol), triethylamine (1.80 ml, 12.9 mmol) and toluene (10 ml) was refluxed under nitrogen atmosphere for 30 hrs. The reaction mixture was concentrated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (2:1, v/v) and recrystallized from ethyl acetate-isopropylether to give the titled compound (0.89 g, 30%).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 30 hrs
  2. concentrationThe reaction mixture was concentrated
  3. washeluted with ethyl acetate-hexane (2:1
  4. customv/v) and recrystallized from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-0d40247de0f64bc3a5a469e787a0f09e
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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