Acetic Acid → Methyl 4-cyanobenzenecarboximidate

HRID 1588571Notes

Reaction equation

HRID 1588571 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+].[C:14](O)(=[O:16])C>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[NH:10])[O:16][CH3:14])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 121721,4-DicyanobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 19734579Methyl 4-cyanobenzenecarboximidateYield 706.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-dicyanobenzene (6.41 g, 50 mmol) was suspended in methanol (100 ml), and sodium methoxide (0.27 g, 5.0 mmol) was added. The mixture was stirred at room temperature for 22 hours. After the reaction was completed, acetic acid (0.31 g, 5.1 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Dichloromethane (50 ml) and diethyl ether (50 ml) were 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 4-cyanobenzenecarboximidate (5.77 g) as colorless powder.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionDichloromethane (50 ml) and diethyl ether (50 ml) were 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-600dc1fb03824929a6db2be2fae9990c
Source dataset
uspto-grants-1993_06
Patent number
US05223508

Reaction notes

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