The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: Vibrating_Lights on September 21, 2002, 02:09:00 AM

Title: Thionyl Chloride
Post by: Vibrating_Lights on September 21, 2002, 02:09:00 AM
Could Thionyl Chloride be used in the place of phosphourous oxychloride with lysergic acid and diethylamine??
Vl_
So much game I could sell a hooker some pussy
Vl_
Title: No.
Post by: Rhodium on September 21, 2002, 06:50:00 AM
No.
Title: why not?
Post by: goiterjoe on September 21, 2002, 10:15:00 PM
Shulgin said it could be with reduced yeilds in TIHKAL.
All paths are the same: they lead nowhere
Title: Exactly where? My comment above was more acually ...
Post by: Rhodium on September 22, 2002, 03:55:00 AM
Exactly where?

My comment above was more acually meaning "if you are asking such a question, then you better nit picard. Soalana Auorveda.
Title: couldn't agree more.
Post by: yellium on September 22, 2002, 08:04:00 AM
couldn't agree more.
Title: TIHKAL #26, p.492 3rd paragraph
Post by: goiterjoe on September 22, 2002, 09:50:00 AM
"The earliest synthesis of LSD involved the use of an azide intermediate (the original Hofmann process, 1955), mixed anhydrides with triflouroacetic anhydride (1956) or sulfuric anhydride (SO3-DMF on the lithium salt, 1959), with the peptide condensation agent N,N'-carbonyldiimidazole (1960), or with the acid chloride as the active intermediate with POCl3, PCl5, or thionyl chloride (1963) or just phosphorus oxychloride (1973).  Most methods are faulted due to excessive moisture sensitivity, generation of side-products, or epimerization or inversion of the 8-position carbon to form d-iso-LSD.  The POCl3 procedure is clean and fast, and is the preferred process today for the synthesis of a wide variety of substituted lysergamides."


All paths are the same: they lead nowhere
Title: In Re 2 Vibrating_Lights:
Post by: neuromodulator on September 22, 2002, 05:56:00 PM
Yes, absolutely.
Yes, absolutely.
Yes, absolutely.

PERIOD

If you don't believe me, ask my old Professor Dr. Garst. 

Keep in mind, however, that he was not actually doing what this thread is talking about of course.  The physics is the same though, kiddies.

R-CO-OH + ClSOCl --> R-CO-Cl + SO2(g) + HCl

R-CO-Cl + N-(Et)2 --> R-CO-N-(Et)2 + Cl-
Title: HCL
Post by: Vibrating_Lights on September 23, 2002, 02:41:00 PM
Would any inprovisions have to be made t oneutralize the HCL as it is formed.  How sensative is the lysergic molocule to HCl.  HCL is also formed in the p oxychloride synth.  If this is a problem then perhaps the rx could take place in Pyridine so the HCl is neutralized as it is formed. ????? Any thing is possible if you dream it long enough.
Vl_ ;)
So much game I could sell a hooker some pussy
Vl_
Title: probably just keep it anhydrous
Post by: goiterjoe on September 23, 2002, 03:09:00 PM
You probably just need to make sure everything stays anhydrous so that the HCl will just vent off.  that's probably why they mentioned the reactions being water sensitive.
All paths are the same: they lead nowhere
Title: nowhere --> erehwon
Post by: TheRampartLion11 on September 25, 2002, 02:16:00 PM
Title: acid chlorides
Post by: Vibrating_Lights on September 26, 2002, 05:29:00 AM
It is important to keep the rxn anhydrous cause the acid chlorides are reactive with water. 
So much game I could sell a hooker some pussy
Vl_
Title: POCl3 substitues
Post by: SPISSHAK on October 13, 2002, 08:30:00 PM
I've seen PCL3 And the pentachloride used also.


I like this synthesis that uses bis phenyl dicarbodiimide and diethyl amine it's a lovely mechnism.
Very gentle reation conditions.
As the LSD is being produced the Bisphenyl carbodiamide is coveted to it's carbamate  (I think)
Barring this, just create POCL3 by oxidizing PCL3 with oxygen.
PCL3 is just Red phosphous, Chloine gas (in anhydrous conditions) very exothermic.
Oxidize that to your desired reagent and you will avoid the
Snooping eyes of the dreaded big brother.
Do not purchase   PCL3! It's also used to make organophosphate nerve agents! and will get you in some hot water!
Good luck!
Title: re: probobly just keep it anhydrous
Post by: saline on October 14, 2002, 11:46:00 AM
more importantly, chlorinating reagents such as SOCl2 and POCl3 react with water.

~saline
Title: SPISSHAK
Post by: PrimoPyro on October 15, 2002, 04:52:00 AM

I like this synthesis that uses bis phenyl dicarbodiimide and diethyl amine it's a lovely mechnism.
Very gentle reation conditions.



Do you have a link or anything to this synthesis you speak of? I am interested in reading more about this!

PrimoPyro

Firm supporter of the "Purge The Couch!" movement. Vote for the purge today.
Title: pyBOP
Post by: Lilienthal on October 15, 2002, 01:41:00 PM
Check also

Post 355652 (https://www.thevespiary.org/talk/index.php?topic=12853.msg35565200#msg35565200)

(Cyrax: "Nice, they use the pyBOP coupling reagent, which ...", Tryptamine Chemistry) for using pyBOP as a coupling reagent instead of diphenylcarbodiimide.