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Topic: Vinyl amides synthesis -  (Read 954 times)

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Offline Pie

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Vinyl amides synthesis -
« on: November 01, 2019, 12:58:04 PM »
I'm reacting vinyl acetate and n-methylacetamide to make n-vinyl-n-methylacetamide using DMAP catalyst.   I've been trying to find a mechanism for hours without any luck. 

I'm trying to find some insight on how to optimize the reaction, besides brute force optimization.   When run with 1mol VA, 1mol NMA, and 0.5mol DMAP the product looks like black oil (which is expected)... I don't get full conversion and I end up with a bunch of impurities I don't know what they are.  If I let the reaction go for days, the vinyl acetate will disappear, and the NMA and DMAP will remain (with product and biproduct). 

Any insights? 

Thanks.
Pie.

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