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(a) Shvedov, V. I.; Mezentseva, M. V.; Grinev, A. N. Khim. Geterotsikl. Soedin. 1975, 9, 1217.
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0040878545
-
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note
-
This mechanism was originally proposed by Cleland and Niemann (see ref 9a); it only applies to the Dakin-West reaction of primary amino acids.
-
-
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25
-
-
0040284216
-
-
note
-
For a typical lab-scale experiment in milligram or low-gram range, the amount of carbon dioxide evolved is certainly too small to be of any concern. Hence, there is no need for an alternative procedure to the Dakin-West reaction on lab scale.
-
-
-
-
27
-
-
0040284217
-
-
note
-
Safety remark: malonodinitrile decomposes autocatalytically at elevated temperatures with an adiabatic temperature rise in excess of 1000 °C! The initiation phase of the decomposition is shortened by bases. For these reasons, when performing this type of pyrrole condensation reactions on large scale, malonodinitrile should be the component being added to the sodium hydroxide solution rather than the opposite way to avoid a possible run-away reaction.
-
-
-
-
28
-
-
0040878543
-
-
note
-
Bulk substance was stored in barrels which were flushed with nitrogen to avoid pyrrole oxidation.
-
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29
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84985264907
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See, for example: Pichler, H.; Folkers, G.; Roth, H. J.; Eger, K. Liebigs Ann. Chem. 1986, 9, 1485.
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0001903116
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Bhadti, V.S.J.5
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35
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0039692513
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U.S. Patent 2,684,976, 1954
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Glickman, A. S. U.S. Patent 2,684,976, 1954.
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Glickman, A.S.1
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36
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0039100269
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note
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This interpretation was later confirmed by applying the final, optimized procedure to different anilines: only those which gave pyrrolopyrimidines poorly soluble in ethanol and which were therefore precipitating from the reaction mixture could be prepared by this procedure.
-
-
-
-
37
-
-
0040878540
-
-
note
-
NMR investigations on the synthesis of iminoester 4b had shown earlier, that at lower temperature, amidine 4c was the predominant product in the mixture, and only by heating above 120 °C and with excess orthoformate, could iminoester 4b be obtained.
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38
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84995196749
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For a review on Dimroth rearrangements, see for example: Wahren, M. Z. Chem. 1969, 9(7), 241.
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4243253686
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Krayushkin, M.M.4
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