Beta-Alanine → N-(4-cyanophenyl)-N'-(2-carboxyethyl)urea

HRID 1034266Notes

Reaction equation

HRID 1034266 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].CO.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=1)#[N:12]>C(OCC)(=O)C>[C:11]([C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:21])=[CH:17][CH:18]=1)#[N:12]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 887MethanolHCID 14798Sodium HydroxideHCID 1703804-Cyanophenyl isocyanate

Product 1

HCID 3018502N-(4-cyanophenyl)-N'-(2-carboxyethyl)ureaYield 61.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen blanket, a mixture of β-alanine (4.4 g; 49 mmoles), sodium hydroxide (2.0 g; 50 mmoles) and methanol (300 ml) was added rapidly to a suspension of 4-cyanophenylisocyanate (8.0 g; 55 mmoles) in ethyl acetate (300 ml). The mixture was stirred at 40° C. for 15 hrs and the volume was reduced to about 150 ml by distillation at reduced pressure. The solid was filtered off, washed with ethyl acetate and dried to yield 7 g of crude product. FAB-MS: MH+=232.

Workup

  1. distillationthe volume was reduced to about 150 ml by distillation at reduced pressure
  2. filtrationThe solid was filtered off
  3. washwashed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-02df9b2501e04e6084da26d6c336e844
Source dataset
uspto-grants-1994_05
Patent number
US05314902

Reaction notes

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