Ethyl formate → N-(2-Methoxy-2-methylpropyl)formamide

HRID 1607344Notes

Reaction equation

HRID 1607344 reaction equation
[CH3:1][O:2][C:3]([CH3:7])([CH3:6])[CH2:4][NH2:5].[CH2:8]([O:10]C=O)C>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:8]([NH:5][CH2:4][C:3]([O:2][CH3:1])([CH3:7])[CH3:6])=[O:10]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 117891412-Methoxy-2-methylpropan-1-amine

Product 1

HCID 14773962N-(2-Methoxy-2-methylpropyl)formamideYield 93%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

To a stirred solution of 2-methoxyisobutylamine (16.4 g, 0.16 mol) and a catalytic amount of p-toluenesulphonic acid (75 mg) at 0° C. was added slowly ethylformate (11.79 g, 12.92 ml, 0.16 mol). After the slightly exothermic reaction ceased, the solution was refluxed for 16 hours, and distilled through a Vigreux column to give 19.36 g (93%) of N-formyl-2-methoxyisobutylamine, bp 74° C./15 mm.

Workup

  1. customAfter the slightly exothermic reaction
  2. temperaturethe solution was refluxed for 16 hours
  3. distillationdistilled through a Vigreux column

Sources & evidence

ORD record
ord-d9c0f9cda4be4c88928de59486e2b9b1
Source dataset
uspto-grants-1989_09
Patent number
US04864051

Reaction notes

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