The Preparation of Some Monoalkyl- and Symmetrical Dialkylethylenediamines

Abstract

Vol. G8ing point determination with authentic 2,4-methylenexylitol caused no depression of this value. The yield was 2.8 g. (889$). The series of reactions constitutes a definitive proof that monomethylene-gluco-gulo-heptitol is 3,5-methylene-gluco-Qulo-heptitol.Although the expected dialdehydo oxidation product from 3,5-methylene-gluco-guZo-heptitol could not be crystallized, i t was isolated in a separate experiment in the Form of its di( phenylhydrazone). The latter compoui~d crystallized from 30 parts of alcohol as small, light yellou plates which melted with decomposition a t 188-190'. SummaryProof is presented that the monobenzylidene-gluco-gulo-heptitol (m. p. 21s') which Emil Fischer discovered is the 3,5-benzylidene acetal. The condensation of gluco-gulo-heptitol with formaldehyde also gives a high yield of a monoacetal which proves to be 3,5-monomethylene-glucocub-heptitol. These 3,5-monoacetals are those to he expected from generalizations relating the configuration of polyhydric alcohols and the structure of their derived benzylidene and methylene acetals.Crystalline 2,4-benzylidene-xylitol and a number of its derivatives have been described. RETHESDA, R~ARYLAND RECEIVED MAY 9, 1946 'CONTRIBUTIOS FROM THE STERLING-\VIS1 IIROP RESEaRCH [NSTIrUTE ]

Quaternization of imidazoline: Unequivocal structure proof

“…Besides, due to the fact that the mass balance was far from quantitative (5) and other products were not identified, no conclusion can be made about the nature of the remaining material. Oxley and Short (7) exhaustively alkylated 2-benzyl-2-imidazoline 11 with methyl p-toluenesulfonate (Scheme V).…”

“…Based on the hydrolysis products, symmetrical structure 4 was proposed. This could easily be rationalized by resonance stability (1,5); however, there are a number of unanswered questions. For example, the one pot reaction was conducted in the presence of an excess of base (5).…”

“…This could easily be rationalized by resonance stability (1,5); however, there are a number of unanswered questions. For example, the one pot reaction was conducted in the presence of an excess of base (5). But the imidazolines are known to hydrolyze in the presence of aqueous base (6).…”

2‐Alkylidenimidazolidine – Synthese, Basizität, 1H‐ und 13C‐NMR‐Spektren

“…d = 10.8 (1.88 g 8f, 1.84 g MeI, 10 ml THF). d = 46.2 (8.70 g Sg, 7.87 g MeI, 30 ml THF). Ethyl-4,5-dihydro-f-methyl-3-phenylimidazolium-iodid (2q): 4,5-Dihydro-f-methyl-3-phenyl-2-propylimidazolium- Dihydro-f-phenyl-2-propyl-fH-imidazo1(8g) Dihydro-f ,3-dimethyl-2-(2-methylpropyl) imidazolium-iodid (2d): c = 18.9 (2.39 g 712, 0.454 g NaH, 6.44 g MeI).…”

Αδαμαντανικές Ιμιδαζολίνες Και Οξαζολίνες Φαρμακολογικού Ενδιαφέροντος

“…(ε) με αντίδραση με αμίδια Η αντίδραση αναφέρεται σε αρυλακεταμίδια 191 σε θερμοκρασία 150-200 0 C και σε ορισμένα θειαμίδια192 . στ) με αντίδραση με νιτρίλια193 Μολονότι η αντίδραση πραγματοποιείται και με τις ελεύθερες βάσεις των διαμινών, καλύτερες αποδόσεις επιτυγχάνονται με τα άλατα των διαμινών και ιδιαίτερα τα θειικά194 .Ακόμη και Ν-υποκατεστημένες αμιδίνες παρουσία π-τουολοσουλφονικού οξέος δίνουν 2-ιμιδαζολίνες195 .2.Από Ν-μονοακυλοκαι Ν,Ν'-διακυλοδιαμίνεςΗ 2-μεθυλο-2-ιμιδαζολίνη παρασκευάζεται με αφυδάτωση και κύκλωση από τη Ν,Ν'-διακετυλοαιθυλενοδιαμίνη με απόδοση 94% παρουσία καταλυτικής ποσότητας μαγνησίου σε λεπτό διαμερισμό196 .Η σύνθεση των 2-μη υποκατεστημένων ή 2-μεθυλοϊμιδαζολινών της παρούσας διατριβής πραγματοποιείται με συμπύκνωση 1,2-διαμινών με άλατα αμιδινών203 :…”