Butyl bromide → N-Butyl-N-cyanoacetamide

HRID 465153Notes

Reaction equation

HRID 465153 reaction equation
[C:1]([NH:4][C:5]#[N:6])(=[O:3])[CH3:2].[Na].[CH2:8](Br)[CH2:9][CH2:10][CH3:11]>CN(C)C=O>[CH2:8]([N:4]([C:5]#[N:6])[C:1](=[O:3])[CH3:2])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 8002Butyl bromideHCID 57358861Sodium acetylcyanamide

Product 1

HCID 20261953N-Butyl-N-cyanoacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

221 g (2.085 mols) of sodium acetylcyanamide are dissolved in 500 ml of dimethylformamide at 90° C., the mixture is allowed to cool to 70° C. and 285.6 g (2.085 mols) of n-butyl bromide are then added dropwise at 70° C. in the course of 11/2 hours. The mixture is allowed to after-react at 70° C. for 10 hours, and the NaBr which has precipitated is filtered off with suction and the entire distillable constituent is removed from the filtrate by vacuum distillation. Fractional distillation of this distillate over a packed column 60 cm high gives 216.4 g (74.1% of theory) of pure product of boiling point 105° C./34 mbar.

Workup

  1. customto after-react at 70° C. for 10 hours
  2. customthe NaBr which has precipitated
  3. filtrationis filtered off with suction
  4. customthe entire distillable constituent is removed from the filtrate by vacuum distillation
  5. distillationFractional distillation of this distillate over a packed column 60 cm
  6. customhigh gives 216.4 g (74.1% of theory) of pure product of boiling point 105° C./34 mbar

Sources & evidence

ORD record
ord-758e22b5fb2d4c948d085665ad77538c
Source dataset
uspto-grants-1985_10
Patent number
US04550203

Reaction notes

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