Cyanogen Bromide → 2,2-Diethoxyethylcyanamide

HRID 615259Notes

Reaction equation

HRID 615259 reaction equation
[N:1]#[C:2]Br.[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[CH2:8][NH2:9])[CH3:5]>CCOCC>[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[CH2:8][NH:9][C:2]#[N:1])[CH3:5]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 695242,2-Diethoxyethylamine

Product 1

HCID 133930082,2-DiethoxyethylcyanamideYield 110%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of cyanogen bromide (2.12 g., 0.02 moles) in ether (20 ml.) was added dropwise over 35 minutes to a stirred ice-cooled solution of aminoacetaldehyde diethyl acetal (5.32 g., 0.04 moles) in ether (20 ml.). During this addition a white precipitate was formed. The resulting suspension was stirred at 0° C. for a further hour, filtered and the filtrate evaporated to dryness under reduced pressure to give 2,2-diethoxyethylcyanamide (3.47 g., 110%) as a colourless oily liquid having the following n.m.r. spectrum in CDCl3 : 1.24 (t, 6H); 3.1 (d, 2H); 3.65 (m, 4H); 4.0 (br s, 1H); 4.57 (t, 1H).

Workup

  1. additionDuring this addition a white precipitate
  2. customwas formed
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1a06b7eedd66420784e192ca96810530
Source dataset
uspto-grants-1985_02
Patent number
US04497949

Reaction notes

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