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

HRID 70051Notes

Reaction equation

HRID 70051 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). 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-7a58ee07e7d14b298d77e0f66ce52043
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

Loading…