Thionyl Chloride

[Vibrating_Lights]

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_

[Rhodium]

No.

[goiterjoe]

Shulgin said it could be with reduced yeilds in TIHKAL.
All paths are the same: they lead nowhere

[Rhodium]

Exactly where?

My comment above was more acually meaning "if you are asking such a question, then you better nit picard. Soalana Auorveda.

[yellium]

couldn't agree more.

[goiterjoe]

"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

[neuromodulator]

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-

[Vibrating_Lights]

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_

[goiterjoe]

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

[TheRampartLion11]

[Vibrating_Lights]

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_

[SPISSHAK]

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!

[saline]

more importantly, chlorinating reagents such as SOCl2 and POCl3 react with water.

~saline

[PrimoPyro]

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.

[Lilienthal]

Check also

Post 355652

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