Methyl Acetate → methyl 4-nitrobenzimidate

HRID 1244542Notes

Reaction equation

HRID 1244542 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12](OC)(=[O:14])C>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8](=[NH:9])[O:14][CH3:12])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6584Methyl AcetateHCID 120904-Nitrobenzonitrile

Product 1

HCID 4326715methyl 4-nitrobenzimidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Part A: 4-Nitrobenzonitrile (5.4 g, 36.5 mmol) was dissolved in 200 mL of anhydrous methyl acetate and 20 mL of MeOH. The whole mixture was cooled to 0° C. and bubbled with dry HCL gas for 1 hour. The resulting mixture was placed at 5° C. for 12 hours, the solvent was removed to obtain 5.8 g of methyl 4-nitrobenzimidate as its HCl salt.

Workup

  1. custombubbled
  2. customwith dry HCL gas for 1 hour
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-83d01c69039f43258e1cf79ef71734e0
Source dataset
uspto-grants-2006_10
Patent number
US07122557B2

Reaction notes

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