Cyanogen Bromide → N-(2,2-diethoxyethyl)carbodiimide

HRID 63224

반응식

HRID 63224 반응식
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].[N:10]#[C:11]Br>CCOCC.CCCCCC>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][N:6]=[C:11]=[NH:10])[CH3:2]

참가 물질

5

반응물 2

HCID 10476Cyanogen BromideHCID 695242,2-Diethoxyethylamine

생성물 1

HCID 10749464N-(2,2-diethoxyethyl)carbodiimide수율 45%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

A solution of the aminoacetaldehyde diethyl acetal (5.32 g, 40 mmol) in ether (20 mL) was added to a suspension of CNBr (4.22 g, 40 mmol) in hexane (20 mL) at RT. The reaction mixture was stirred at RT overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Flash chromatography of the concentrated residue afforded 2.82 g (45%) of the N-(2,2-diethoxyethyl)carbodiimide (a). 1H NMR (500 MHz, CDCl3): 4.58 (t, J=5.5 Hz, 1H), 3.85 (br s, 1H), 3.73 (m, 2H), 3.56 (m, 2H), 3.16 (J=5.5 Hz, 2H), 1.23 (t, J=7.0 Hz, 3H), MS: 156.8 (M−H)−; 180.9 (M+Na)+.

후처리

  1. customThe solid was removed by filtration
  2. washwashed with ether
  3. concentrationThe combined filtrate was concentrated

출처 및 근거

ORD 기록
ord-70e8f860d55447f2a9b73b67dce16002
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447049B2

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