Reaction #91502

Reaction equation

aminoacetaldehyde diethyl acetal

CNBr

→

N-(2,2-diethoxyethyl)carbodiimide

Yield 45.0%

Solvents

ether

hexane

Conditions

Workup

1. 1
   OtherThe solid was removed by filtration
2. 2
   Washwashed with ether
3. 3
   ConcentrationThe combined filtrate was concentrated

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)+.

Source