1.3‐Dipolare Additionen der Azomethin‐imine an Azomethine, Nitrile und Thiocyanate

Grashey, Rudolf; Leitermann, Herta; Scmidt, Renate; Adelsberger, K.

doi:10.1002/ange.19620741411

Cited by 17 publications

(2 citation statements)

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“…Gaseous reactants were introduced through gas addition tubes; solid reactants were dissolved in a minimum volume of solvent. (12) Recovered yields were about 10% lower if the hexane was not added, owing to partial solubility of the product in diethyl ether. Preparation of Indenyllithium-Ethylenediamine.…”

Section: Methodsmentioning

confidence: 99%

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Lithiated Diamines as Metalating Agents

Beumel¹,

Harris²

1965

J. Org. Chem.

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with sodium bicarbonate and the solution was extracted with ether. When the ether was dried and evaporated, 4.0 g. of white solid, VII, was obtained, (29%). Upon recrystallization from acetone-water, this material melted at 160-160.5°.1.3-Di-p-tolyl-5,5-dimethyl-6-piperidinohydrouracil' (V).-A mixture of p-tolyl isocyanate (13.30 g., 0.10 mole) and 1-piperidinoisobutene (6.95 g., 0.05 mole) was sealed in a thick-walled tube and heated at 110-120°for 20 hr, then at 150°for 3 hr. The glassy solid was taken up in hot acetone to remove it from the tube. Upon evaporation of the acetone, an oil was obtained which did not solidify. The oil was taken up in dry ether and hydrogen chloride gas was passed into it. The hydrochloride precipitated as a white hygroscopic solid. This hydrochloride was then dissolved in a mixture of 3 g. of sodium hydroxide in 15 ml. of methanol and 100 ml. of water. This solution was then stirred with ether for 1.5 hr. After separation, the ether was washed with water, then dried over magnesium sulfate, and evaporated. The residual oil (20 g., 98%) solidified after standing for a week. After several recrystallizations from aqueous acetone, the resulting white solid had m.p. 157-158°; X^¿01 no peaks in 3-µ region, 5.81 (s), 5.94 (s), and 6.18 (w) µ.' Elemental analysis was performed on the picrate. To a solution of 0.526 g. of V in 3.0 ml. of methanol was added 3.0 ml. of a saturated (at 24°) picric acid solution. The mixture was warmed for 5 min. on a steam bath, then allowed to stand at room tempera-

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Section: Methodsmentioning

confidence: 99%

“…of hydrochloric acid and 20 ml. of water was added 12.0 g. (0.0296 mole) of V. The reaction mixture was refluxed for 12 hr. The solid obtained after cooling and filtering weighed 7.6 g. (0.0225 mole, 76%).…”

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confidence: 99%