Toluene → Diisopropylethylamine

HRID 892925

Reaktionsgleichung

Reaktionsgleichung von HRID 892925
[CH3:1]N(CCN(C)C)C.CC[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13].CN(CC)CC.[C:22]1([CH3:28])[CH:27]=CC=CC=1>>[CH:14]([N:11]([CH:22]([CH3:27])[CH3:28])[CH2:12][CH3:13])([CH3:15])[CH3:1]

Komponenten

5

Edukt 4

HCID 1140TolueneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8471TriethylamineHCID 12022Diethylmethylamine

Produkt 1

HCID 81531Diisopropylethylamine

Versuchsvorschrift

Surprisingly, diisopropylethylamine in methylene chloride gave a 59:41 mixture of starting material:2-iodo product (Run #14), and only a trace of the 2-iodo product was observed in toluene under similar conditions. The low solubility of the hydrohalide salts of TMEDA, Et3N and Et2MeN in the above solvents may be responsible for their usefulness as opposed to the poor results with diisopropylethylamine. Precipitation of these hydrohalide salts may remove sufficient acid from the reaction so that the equilibrium is displaced toward product allowing the reaction to proceed to completion.

Aufarbeitung

  1. additiona 59:41 mixture of starting material

Quellen und Nachweise

ORD-Eintrag
ord-ee7ecbde496a44018511101be93ab07d
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05120847

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