Acryloyl chloride → N-(2,2-Dimethoxyethyl)-2-propenamide

HRID 1980216Notes

Reaction equation

HRID 1980216 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].Cl.[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH2:11]>>[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH:11][C:1](=[O:4])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 13140Acryloyl chloride2×HCID 202396922,2-Dimethoxyethanamine hydrochloride

Product 1

HCID 9898899N-(2,2-Dimethoxyethyl)-2-propenamideYield 92%

Procedure

The round bottom flask was suspended in a dry ice-isopropanol bath. When the contents reached 0° C., the acryloylchloride solution was allowed to slowly drip into the flask. Temperature was maintained at 0° to 3° C. over a 40 minute period during which all the acryloylchloride solution had been added. Voluminous white crystals of aminoacetaldehyde dimethylacetal hydrochloride were present in the product. These crystals were removed via filtration. Methoxyhydroquinone (0.1 gram) was added and the filtrate was concentrated by evaporation of the ethyl ether to yield 189 grams of N-(2,2 dimethoxyethyl)acrylamide (92% yield).

Workup

  1. customThe round bottom flask was suspended in a dry ice-isopropanol bath
  2. customreached 0° C.
  3. additionhad been added
  4. customThese crystals were removed via filtration
  5. additionMethoxyhydroquinone (0.1 gram) was added
  6. concentrationthe filtrate was concentrated by evaporation of the ethyl ether

Sources & evidence

ORD record
ord-a6840b3d624e48038ebcd67a5623b092
Source dataset
uspto-grants-1985_04
Patent number
US04508594

Reaction notes

Loading…