Ethyl cyanoacetate → HCID 6840755, compound

HRID 1920619Notes

Reaction equation

HRID 1920619 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]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:10]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][C:12](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:13]1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl ester

Product 1

HCID 6840755HCID 6840755, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (6 g, 35.7 mM) and ethyl cyanoacetate (4 g, 35.4 mM) were dissolved in toluene (10 ml), and triethylamine (5 ml, 35.8 mM) was added to the solution, followed by heating for 7 hours under reflux. After the reaction solution was concentrated, ethanol was added to the residue. The mixture was allowed to stand, and the crystals precipitated were taken out by filtration to give crude crystals. The crude crystals were recrystallized from ethanol to give the title compound as needles (5.4 g, 60.7%).

Workup

  1. temperatureby heating for 7 hours
  2. temperatureunder reflux
  3. concentrationAfter the reaction solution was concentrated
  4. additionethanol was added to the residue
  5. customthe crystals precipitated
  6. filtrationwere taken out by filtration
  7. customto give crude crystals
  8. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-795ecc5514734d7c9011a3ae79b7b61a
Source dataset
uspto-grants-2012_05
Patent number
US08173360B2

Reaction notes

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