Acetone → N-Cyano-N-(propan-2-yl)acetamide

HRID 465152Notes

Reaction equation

HRID 465152 reaction equation
[C:1]([NH:4][C:5]#[N:6])(=[O:3])[CH3:2].[Na].[CH:8](Br)([CH3:10])[CH3:9].CC(C)=O>CN(C)C=O>[CH:8]([N:4]([C:5]#[N:6])[C:1](=[O:3])[CH3:2])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 63582-BromopropaneHCID 57358861Sodium acetylcyanamide

Product 1

HCID 57265092N-Cyano-N-(propan-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

31.8 g (0.30 mol) of sodium acetylcyanamide are dissolved in 75 ml of dimethylformamide at 100° C., and 36.9 g (0.30 mol) of isopropyl bromide are added dropwise in the course of 11/2 hours. The mixture is allowed to afterreact at 100° C. for 3 hours, and then 200 ml of acetone are added and the NaBr which has precipitated is filtered off with suction (28.2 g=0.27 mol). The acetone is then removed on a rotary evaporator and the residue is distilled under a waterpump vacuum in order to isolate all the distillable constituents. Fractional distillation of this distillate over a spinning bank column give 14.3 g (37.8% of theory) of a product of boiling point 107° C./90 mbar which, according to gas chromatography, is a single product.

Workup

  1. customthe NaBr which has precipitated
  2. filtrationis filtered off with suction (28.2 g=0.27 mol)
  3. customThe acetone is then removed on a rotary evaporator
  4. distillationthe residue is distilled under a waterpump vacuum in order
  5. customto isolate all the distillable constituents
  6. distillationFractional distillation of this distillate over a spinning bank column
  7. customgive 14.3 g (37.8% of theory) of a product of boiling point 107° C./90 mbar which

Sources & evidence

ORD record
ord-8d8b3c65995945b696d52b012ebf0941
Source dataset
uspto-grants-1985_10
Patent number
US04550203

Reaction notes

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