Triethylamine → HCID 66873480, compound

HRID 1920620Notes

Reaction equation

HRID 1920620 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]1[CH2:17][CH2:16][N:15]([C:18]([CH2:20][C:21]#[N:22])=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:19]=[C:18]([N:15]1[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]1)[CH:20]=[C:21]1[NH:22][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 847651-(Cyanoacetyl)piperidine

Product 1

HCID 66873480HCID 66873480, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (1.7 g, 10.1 mM) and 1-cyanoacetylpiperidine (2.0 g, 13.1 mM) were dissolved in toluene (5 ml), and triethylamine (2 ml, 14.4 mM) was added to the solution. After heating for 30 hours under reflux, the reaction solution was concentrated to give crude crystals. The crude crystals were recrystallized from ethanol to give the title compound as needles (730 mg, 25%).

Workup

  1. temperatureAfter heating for 30 hours
  2. temperatureunder reflux
  3. concentrationthe reaction solution was concentrated
  4. customto give crude crystals
  5. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-f60b5d4c8a654bcbb206f1fb927335d3
Source dataset
uspto-grants-2012_05
Patent number
US08173360B2

Reaction notes

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