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Topic: Will thionyl chloride work for replacing R-NH2 and/or R-NH-R with Cl?  (Read 10756 times)

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Offline Cesium-137

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Will thionyl chloride work for replacing R-NH2 and/or R-NH-R with Cl?
« on: November 15, 2010, 03:22:23 AM »
Before I go wasting too much quality hood time on failed reactions, does anyone know if I can replace a primary or secondary amine with a chlorine using thionyl chloride? What kind of conditions are necessary for each amine substitution? I would also be interesting in knowing which, if any, functional groups besides OH can be replaced with Cl by SOCl2. Thanks for your expertise!!!
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Offline discodermolide

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Re: Will thionyl chloride work for replacing R-NH2 and/or R-NH-R with Cl?
« Reply #1 on: November 15, 2010, 07:13:06 AM »
Quote from: Cesium-137 on November 15, 2010, 03:22:23 AM
Before I go wasting too much quality hood time on failed reactions, does anyone know if I can replace a primary or secondary amine with a chlorine using thionyl chloride? What kind of conditions are necessary for each amine substitution? I would also be interesting in knowing which, if any, functional groups besides OH can be replaced with Cl by SOCl2. Thanks for your expertise!!!

Amines will react with SOCl2, but not in the manner you are suggesting. You will probably end up with the urea.
SOCl2, reacts with alcohols and carboxylic acids, sulfonic acids, thols, phosphorous acids, that's about it.
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Offline discodermolide

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Re: Will thionyl chloride work for replacing R-NH2 and/or R-NH-R with Cl?
« Reply #2 on: November 15, 2010, 08:34:10 AM »
Quote from: discodermolide on November 15, 2010, 07:13:06 AM
Quote from: Cesium-137 on November 15, 2010, 03:22:23 AM
Before I go wasting too much quality hood time on failed reactions, does anyone know if I can replace a primary or secondary amine with a chlorine using thionyl chloride? What kind of conditions are necessary for each amine substitution? I would also be interesting in knowing which, if any, functional groups besides OH can be replaced with Cl by SOCl2. Thanks for your expertise!!!

Amines will react with SOCl2, but not in the manner you are suggesting. You will probably end up with the (urea).
I meant the bis-sulfinamide, RNS(O)NR'. (sorry)
SOCl2, reacts with alcohols and carboxylic acids, sulfonic acids, thols, phosphorous acids, that's about it.

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Offline MissPhosgene

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Re: Will thionyl chloride work for replacing R-NH2 and/or R-NH-R with Cl?
« Reply #3 on: November 15, 2010, 09:26:18 AM »
Hydrolyze first then make the acid chloride. If you can do acid hydrolysis, that would be best.
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