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

HRID 63224

反応式

HRID 63224 の反応式
[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]

参加物

5

反応物 2

HCID 10476Cyanogen BromideHCID 695242,2-Diethoxyethylamine

生成物 1

HCID 10749464N-(2,2-diethoxyethyl)carbodiimide収率 45%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-70e8f860d55447f2a9b73b67dce16002
出典データセット
uspto-grants-2016_09
特許番号
US09447049B2

関連ノート

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