Über Cyclohexylamine. (II.)

“…Their unknown compound may have been benzyl nitrite. More to the point, Sitka and Rolfes (25) obtained Ar-n i t ro s o-.V-methy 1 evclohexy 1 amine on treatment of Ar,.V-dimethylcyelohexylaminc with nitrosyl chloride at zero degrees in dry ether. They did not isolate any other product but reported that the reaction mixture had an odor of formaldehyde.…”

Section: Other Workmentioning

confidence: 97%

The reaction of tertiary amines with nitrous acid

Hein¹

1963

J. Chem. Educ.

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“…Calc. for CllI-I190?Na: C, 38.64; I-I, 8 (25), yield 37 mg (10%). Analysis and inelting point indicated it to be N-acetyl cyclol~exylan~ii~e, and this mas confir~ned by preparation of an authentic sample and comparison of the infrared spectra.…”

Section: Cetylation Of Gz~anidine Free Bases Witlz Ethyl Acetatementioning

confidence: 98%

Guanidine Compounds: Iv. Acetylation of Some Alkyl-Substituted Guanidines With Acetic Anhydride and Ethyl Acetate

Greenhalgh¹,

Bannard²

1961

Can. J. Chem.

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'fhc acctylatiorl of some mono-, N,N-, and N,Nf-diallcylguanidi~les was studied using c~h y l acetate and acetic anhydride. Except for the N,N-diallcylguanidines, the action of ethyl acetate on the free bases gave monoacetyl derivatives. Acetic anhydride with the acetate salts gave diacetyl derivatives with monoalliylguanidines, acetamido-1,3,5-triazines with N,N-dialkylguanidi~les, and unstable di-and tri-acetyl derivatives with N,N'-diallcylguanidines. The assignment of symmetrical structures to the mono-and tri-acetyl derivatives and an asymmetrical structure to the diacetyl Gerivatives was supported by nuclear magnetic resonance spectra. The ultraviolet spectra of the monoacetyl derivatives exhibited one peal; in the region 230-235 mp whilst the diacetyl derivatives showed two pealcs in the regions 220-230 mp ancl 253-263 mp. Some comments are made on the infrared spectra of these compounds.In an earlier paper in this series Cockburn and Bannard (1) reported the for~nation of amino-(I) and acetarnido-s-triazines (11) on acetylation of alkylguanidine saIts under vigorous conditions. R'R" I. R = H ; R', R" = H or all;yl 11. R = CH3CO; R', R" = H or allcyl 111. R = CH3CO; R', R" = CH, Iiyabinin (2) had previously show11 that the products obtained on acetylation of guanidine acetate were dependent on the conditions used. Under mild conditions, an acetylated guanidine derivative was obtained rather than an s-triazine derivative. The present study, in which the acetylation of several mono-, N,N-, and N,N1-diallcylguanidines with ethyl acetate and acetic anhydride was esamined, revealed that the type of allcyl substitution also influenced the product obtained. T h e opportunity was talcen t o examine the infrared and ultraviolet spectra of the acetylated guanidines isolated.Various conditions for the acetylation of trans-2-guanidocyclohexanol with acetic anhydride were examined t o determine which gave the highest yield of acetylated products. T h e addition of sodiunl acetate did not influence the yields and was therefore omitted, since it merely complicated isolation of the products. I t was found that a shorter time of heating a t 100' than that previously employed for the acetylation of guanidine (3) was beneficial, since even the relatively stable diacetyl derivatives were degraded or cyclized on prolonged heating with acetic anhydride a t this temperature.

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Über Cyclohexylamine. (II.)

Cited by 42 publications

References 3 publications

Substituted Heterocyclic Thioureas I

Substituted Heterocyclic Thioureas I

The reaction of tertiary amines with nitrous acid

Guanidine Compounds: Iv. Acetylation of Some Alkyl-Substituted Guanidines With Acetic Anhydride and Ethyl Acetate

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