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Topic: Conversion of N-ethylacetamide to N,N-dimethylethanamine  (Read 925 times)

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Offline Sgrambble

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Conversion of N-ethylacetamide to N,N-dimethylethanamine
« on: August 24, 2023, 07:33:24 AM »
is there a way to convert N-ethylacetamide to N,N-dimethylethanamine?? Im doing a first year organic chemistry course and this reaction was shown on the whiteboard as one step. Although this course is relatively introductory, out of interest I started investigating and I know it's not going to be one step. There's likely going to be reductions, methylation (or Dimethylation) and more but I've been trying to figure it out for ages and I can't for the life of me. Anything would be greatly appreciated- I will attach images of the 2 mentioned chemicals :)

Offline Hunter2

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Re: Conversion of N-ethylacetamide to N,N-dimethylethanamine
« Reply #1 on: August 24, 2023, 07:58:19 AM »
N-Ethyl acetamid to Ethylamin , crack with NaOH.
Ethylamin react with 2 mol Methylbromide

Or use Hofmann reaction
« Last Edit: August 24, 2023, 08:10:52 AM by Hunter2 »

Offline Sgrambble

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Re: Conversion of N-ethylacetamide to N,N-dimethylethanamine
« Reply #2 on: August 24, 2023, 08:38:37 AM »
will the Hoffman rearrangement work if the amide has just one hydrogen bonded to the nitrogen? From what I believe, by definiton the Hoffman Rearrangement requires a primary amide which only has one carbon bonded to the NH2. I may be wrong as I am only a first year chemist and I'll take critique with open arms but I've had a look around and it seems to be the case.
« Last Edit: August 24, 2023, 09:08:42 AM by Sgrambble »

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