Acetic Acid → Methyl 2-thiophenecarboximidate

HRID 327134Notes

Reaction equation

HRID 327134 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)#[N:2].C[O-].[Na+].[C:11](O)(=[O:13])C>CO>[S:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:1](=[NH:2])[O:13][CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 660872-ThiophenecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 398427Methyl 2-thiophenecarboximidateYield 817.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-cyanothiophene (5.46 g, 50 mmol) was dissolved in methanol (25 ml), and sodium methoxide (0.27 g, 5 mmol) was added. The mixture was stirred at room temperature for 18 hours. After the reaction was completed, acetic acid (0.33 g, 5.5 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Diethyl ether (40 ml) was added to the concentrated residue, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product of methyl 2-thiophenecarboximidate (6.35 g) as a yellow oil.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionDiethyl ether (40 ml) was added to the concentrated residue, and insolubles
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bcf260765b9443cc9416a9fa725d3fc9
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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