L42L (Stranger)
02-18-03 20:35
No 409482
       ?'s acetonitrile synth?  Bookmark   

Saw this on the bathroom wall in the grout; gramine methosulfate ->NaCN->I-3-acetonitrile. Can some bee tell me about the gramine methosulfate.

To the point, how does one get from indole or gramine to gramine methosulfate.

Thanks Beez
lurk 		 
 
 
 
    Rhodium
(Chief Bee)
02-18-03 21:23
No 409501
       Gramine Methosulfate  Bookmark   

 
 
 
 
    L42L
(Stranger)
02-19-03 00:06
No 409557
       Cool!  Bookmark   

Neat-o! This might be as simple as I hoped. Thanks for your response, Rhod. Here's the dirt;

A solution of gramine methosulfate (30.0g, .10 mol) and NaCN (15.0g, 0.30 mol) in water (300ml) was heated to 65-70 C for one hour. A colurless oil separated as the reaction proceeded. The solution was cooled and saturated with Na2SO4 and extracted with ethyl ether (400ml). The ether was removed in vacuo and the residue purified by high vacuum distillation to give the product in 94% yield. Sit on it Potzee.

On my way out of his office the Fonz stuck his thumbs up and said,
"J. Thesing and F Schulde. Cem. Ber. 85, 324 (1952)"
He wouldn’t say if that’s who scrawled it in the grout of not.
Sooooo... Can some bee direct me to the nearest dimethyl sulfate synth, sure seems easy. Did a quick search and didn’t find much, just a thread entitled:

  Trimethyl phosphate methylation of 4-alkyl1,4-DHOB

Comments are appreciated,
thanks bees !
lurk
  
 
 
 
    Rhodium
(Chief Bee)
02-19-03 00:52
No 409568
       How's your spelling?  Bookmark   

Do you use the same search engine as I do? With TFSE at https://www.the-hive.ws/forum/searchx.pl I found 85 posts with "dimethyl sulfate" in the subject field and 276 posts with "dimethyl sulfate" in the body. You also get 78 hits on the misspelling "dimethylsulfate", 87 hits on the old british spelling "dimethyl sulphate" and even on the misspelling "dimethylsulphate" of the latter you get 18 hits in return. 		 
 
 
 
    Rhodium
(Chief Bee)
02-20-03 18:01
No 410166
       Tryptamine & IAA via a Gramine quaternary salt
(Rated as: excellent) 		 Bookmark   

Besides, the structure of gramine methosulfate is actually drawn in the article you referenced:

Notiz über die präparative Darstellung von Heteroauxin und Tryptamin
Jan Thesing & Felix Schülde
Chem. Ber. 85, 324-327 (1952) (../rhodium/pdf /heteroauxin.pdf)