Acetic Acid → N-(2-cyano-3-methylbutanoyl)urea

HRID 2289186Notes

Reaction equation

HRID 2289186 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]([NH2:9])=[O:8])=[O:5])#[N:2].[CH3:10][C:11]([CH3:13])=O.C(O)(=O)C.C([O-])(=O)C.[NH4+]>CN(C)C=O.[C].[Pd]>[C:1]([CH:3]([CH:11]([CH3:13])[CH3:10])[C:4]([NH:6][C:7]([NH2:9])=[O:8])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 74055Acetamide, N-(aminocarbonyl)-2-cyano-HCID 517165Ammonium Acetate

Product 1

HCID 9793952N-(2-cyano-3-methylbutanoyl)ureaYield 85.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Cyanoacetylurea (78.6 g) was suspended in N,N-dimethylformamide (154.9 ml), and acetone (48.8 g), acetic acid (7.2 g) and ammonium acetate (4.6 g) were added. This suspension was subjected to catalytic hydrogenation in the presence of 10% palladium carbon (3.1 g, 50% wet product) under hydrogen pressure at 10 kg/cm2 and at 25° C. for 4 hours. The reaction mixture was heated to 70° C. to dissolve an insoluble matter, and the catalyst was filtered off. Water (390 ml) was added to the obtained filtrate to allow precipitation of crystals. The crystals were collected by filtration to give crystals of N-(2-cyano-3-methylbutanoyl)urea (yield 89.7 g).

Workup

  1. dissolutionto dissolve an insoluble matter
  2. filtrationthe catalyst was filtered off
  3. additionWater (390 ml) was added to the obtained filtrate
  4. customprecipitation of crystals
  5. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-7b78d784562747a4a8328ce3996de126
Source dataset
uspto-grants-2000_07
Patent number
US06090970

Reaction notes

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