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

HRID 2289184Notes

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+]>C(O)(C)C.[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

Conditions

Temperature: 80 °C

Procedure

Cyanoacetylurea (38.7 g) was suspended in isopropanol (77.4 ml), and acetone (24.6 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 8 hours. The reaction mixture was heated to 80° C. for 1 hour, and the catalyst was filtered off. Water (150 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 21.7 g).

Workup

filtrationthe catalyst was filtered off
additionWater (150 ml) was added to the filtrate
customprecipitation of crystals
filtrationThe crystals were collected by filtration

Sources & evidence

ORD record: ord-89700ca4f9024da8a5130b4da667becb
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090970

Reaction notes

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