Isopropylamine → N-Isopropylmethacrylamide

HRID 903516

Reaction equation

HRID 903516 reaction equation
[C:1]([O:6]C)(=O)[C:2]([CH3:4])=[CH2:3].[CH:8]([NH2:11])([CH3:10])[CH3:9]>Cl.C(N)(C)C>[CH:8]([NH:11][C:1](=[O:6])[C:2]([CH3:4])=[CH2:3])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 6658Methyl Methacrylate2×

Product 1

HCID 83698N-IsopropylmethacrylamideYield 69.5%

Reagents, catalysts & solvents 1

HCID 64321372-Propanamine, hydrochloride (1:1)Catalyst

Procedure

500 g (5 mols) of methyl methacrylate, 325 g (5.5 mols) of isopropylamine, and 12.4 g (0.13 mol) of isopropylamine hydrochloride were reacted in the presence of 0.03 mol of ferric acetylacetonate for 21/2 hours in a steel autoclave at 220° C. The pressure increased to a maximum of 18 atmospheres. The methyl methacrylate reacted to the extent of 80% and gave 442 g of N-isopropylmethacrylic acid amide (corresponding to a 68% yield referred to the methyl methacrylate used).

Workup

  1. temperatureThe pressure increased to a maximum of 18 atmospheres

Sources & evidence

ORD record
ord-b6193f641d56497c9298501d403d530e
Source dataset
uspto-grants-1980_10
Patent number
US04228102

Linked notes

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