sonogashira
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N-chlorosuccinimide
I'm looking for a procedure for the chlorination of succinimide to give NCS. Reading through March (6th Edition, p849) it suggests that succinimide is
chlorinated with NaOCl to give NCS (NaOBr gives NBS), but no reference is given!
From searching Google I've found a reference to the Merck Index from the sigmaaldrich website: Merck 13, 2183 (I downloaded this
edition from references some time ago but have never been able to get it to work!)
Searching the literature has been hampered by the hundreds of uses for NCS.. needle in a haystack!
I would appreciate it if someone could assist me with either obtaining this Merck entry, or better still directing me towards a paper on its
preparation.
With kind regards.
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S.C. Wack
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Beilstein would probably make that search a lot easier if it is in a library near you.
Shirley has a preparation from a 1901 Ber. article. This uses 8% potassium hypochlorite.
Well, the Merck file does work.
Monograph Number: 2183
Title: N-Chlorosuccinimide
CAS Registry Number: 128-09-6
CAS Name: 1-Chloro-2,5-pyrrolidinedione
Additional Names: succinchlorimide
Molecular Formula: C4H4ClNO2
Molecular Weight: 133.53.
Percent Composition: C 35.98%, H 3.02%, Cl 26.55%, N 10.49%, O 23.96%
Literature References: Prepn from succinimide: Hirst, Macbeth, J. Chem. Soc. 121, 2169 (1922); Zimmer, Audrieth, J. Am. Chem. Soc. 76, 3856 (1954).
Crystal structure: Brown, Acta Cryst. 9, 193 (1956); 14, 711 (1961). Toxicity data: Stohlman, Smith, U.S. Publ. Health Repts. 59, 541 (1944).
Properties: Orthorhombic crystals, mp 150-151°. Odor of chlorine. Acid to litmus (1:50 aq soln). One gram dissolves in about 70 ml water, 150 ml
alcohol, 50 ml benzene. Sparingly sol in ether, chloroform, carbon tetrachloride. Liberates iodine from potassium iodide solns, and bromine from
sodium bromide solns. MLD orally in rats: 2.7 g/kg (Stohlman, Smith).
Melting point: mp 150-151°
Toxicity data: MLD orally in rats: 2.7 g/kg (Stohlman, Smith)
Use: Chlorinating agent.
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sonogashira
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| Quote: | Originally posted by S.C. Wack
Shirley has a preparation from a 1901 Ber. article. This uses 8% potassium hypochlorite. |
Perfect! I've just downloaded this book and it looks most useful. Many thanks for your assistance.
I wonder if NaOCl would work? Though I guess they have used KOCl for a reason.. might be worth a try though.
Thanks again!
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not_important
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Germany had large natural supplies of potassium salts such as polyhalite, and sylvite, chemists often used the potassium salts instead of the sodium
ones. This caused considerable expense to chemists in other countries when they exactly replicated experiments of the Germans.
Having said that, there are cases where the greater or lesser solubility of the potassium salt makes it preferable over the sodium. The carbonates
are and example of greater solubility, permanganates of lesser (makes it practical to crystallise).
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sonogashira
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Very interesting. I looked up the preparation of NBS as well (great book!) and they've used NaOH, Br2 in a similar procedure so I guess the NaOCl
would be well worth a try!
Thanks for the info!
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