Ethyl cyanoacetate → HCID 6840755, compound

HRID 1007129Notes

Reaction equation

HRID 1007129 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, compound

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 then triethylamine (5 ml, 35.8 mM) was added thereto. After heating under reflux for 7 hours, the reaction solution was concentrated. Ethanol was added to the residues and kept still, and the precipitated crystals were collected by filtration to give crude crystals. The product was recrystallized from ethanol to give the title compound as needle crystals (5.4 g, 60.7%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 7 hours
  3. concentrationthe reaction solution was concentrated
  4. additionEthanol was added to the residues
  5. filtrationthe precipitated crystals were collected by filtration
  6. customto give crude crystals
  7. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-f665cc68b50847f98869259b37b44f04
Source dataset
uspto-grants-2004_09
Patent number
US06794383B2

Reaction notes

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