Toluene → Diisopropylethylamine

HRID 892925

반응식

HRID 892925 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 81531Diisopropylethylamine

실험 절차

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.

후처리

  1. additiona 59:41 mixture of starting material

출처 및 근거

ORD 기록
ord-ee7ecbde496a44018511101be93ab07d
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05120847

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