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

HRID 2289187Notes

Reaction equation

HRID 2289187 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]([NH2:9])=[O:8])=[O:5])#[N:2].[C:10](O)(=O)[CH3:11].[C:14]([O-])(=O)C.[NH4+]>CC(C)=O.[C].[Pd]>[C:1]([CH:3]([CH:10]([CH3:11])[CH3:14])[C:4]([NH:6][C:7]([NH2:9])=[O:8])=[O:5])#[N:2]

Participants

6

Reactant 3

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

Product 1

HCID 9793952N-(2-cyano-3-methylbutanoyl)ureaYield 889.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 180AcetoneSolvent

Procedure

Cyanoacetylurea (51.6 g) was suspended in acetone (516 ml), and acetic acid (4.8 g) and ammonium acetate (3.2 g) were added. This suspension was subjected to catalytic hydrogenation in the presence of 5% palladium carbon (4.1 g, 50% wet product) under normal pressure at 40° C. for 5 hours. The reaction mixture was refluxed under heating to dissolve an insoluble matter, and the catalyst was filtered off. The obtained filtrate was concentrated to a half, and water (258 ml) was added to the filtrate to allow precipitation of crystals. The crystals were collected by filtration to give crystals of N-(2-cyano-3-methylbutanoyl)urea (yield 62.5 g).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperatureunder heating
  3. dissolutionto dissolve an insoluble matter
  4. filtrationthe catalyst was filtered off
  5. concentrationThe obtained filtrate was concentrated to a half, and water (258 ml)
  6. additionwas added to the filtrate
  7. customprecipitation of crystals
  8. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-0f0102f8891444c7bf276eecf94c4356
Source dataset
uspto-grants-2000_07
Patent number
US06090970

Reaction notes

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