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

HRID 63224

Reaction equation

HRID 63224 reaction equation
[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]

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 695242,2-Diethoxyethylamine

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-70e8f860d55447f2a9b73b67dce16002
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Linked notes

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