2-Thiophenecarboxaldehyde → 2-Cyano-3-thiophen-2-yl-thioacrylamide

HRID 1991450Notes

Reaction equation

HRID 1991450 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[C:8]([CH2:10][C:11]([NH2:13])=[S:12])#[N:9]>CO>[C:8]([C:10](=[CH:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:11](=[S:12])[NH2:13])#[N:9]

Participants

4

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 14162772-Cyanoethanethioamide

Product 1

HCID 27298552-Cyano-3-thiophen-2-yl-thioacrylamideYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of thiophene-2-carbaldehyde (20.0 g, 0.18 mol) and 2-cyanothioacetamide (17.8 g, 0.18 mol) in methanol (400 mL), was added neutral Al2O3 (106 g). The suspension was stirred at room temperature for 48 hrs, and then filtered. The solid was washed with methanol and the filtrates were combined and the solvent was then removed by evaporation to afford 2-cyano-3-thien-2-ylprop-2-enethioamide (30 g, 87%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with methanol
  3. customthe solvent was then removed by evaporation

Sources & evidence

ORD record
ord-cee54c3d37bb43fb90f09505385ba61e
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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