Acetic Acid → N-carbamoyl-2-cyano-butanamide

HRID 2289185Notes

Reaction equation

HRID 2289185 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]([NH2:9])=[O:8])=[O:5])#[N:2].[CH:10](=O)[CH3:11].C(O)(=O)C.C([O-])(=O)C.[NH4+]>CN(C)C=O.[C].[Pd]>[C:1]([CH:3]([CH2:10][CH3:11])[C:4]([NH:6][C:7]([NH2:9])=[O:8])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 74055Acetamide, N-(aminocarbonyl)-2-cyano-HCID 517165Ammonium Acetate

Product 1

HCID 224009N-carbamoyl-2-cyano-butanamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Cyanoacetylurea (38.7 g) was suspended in N,N-dimethylformamide (77.4 ml), and acetaldehyde (18.8 ml), acetic acid (3.43 ml) and ammonium acetate (2.31 g) were added. This suspension was subjected to catalytic hydrogenation in the presence of 10% palladium carbon (0.78 g, 50% wet product) under normal pressure at 30° C. for 5 hours. The catalyst was filtered off. Water (350 ml) was added to the filtrate to allow precipitation of crystals. The crystals were collected by filtration to give crystals of N-(2-cyanobutanoyl)urea (yield 24.2 g). 1H-NMR(270 MHz, DMSO-d6)δ 0.99(3H,t), 1.75-1.95(2H,m), 3.86(1H,t), 7.42(2H,br), 10.50(1H,br)

Workup

  1. filtrationThe catalyst was filtered off
  2. additionWater (350 ml) was added to the filtrate
  3. customprecipitation of crystals
  4. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-8d23a97cd3f344fe8dcfee0cb6f83430
Source dataset
uspto-grants-2000_07
Patent number
US06090970

Reaction notes

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