Hydrogen Peroxide → N,N-Diisopropyl-3-carbamoyl-3-phenylpropanamide

HRID 428341Notes

Reaction equation

HRID 428341 reaction equation
[CH:1]([N:4]([CH:17]([CH3:19])[CH3:18])[C:5](=[O:16])[CH2:6][CH:7]([C:14]#[N:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[OH:20]O>CCO.[OH-].[Na+]>[CH:17]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:16])[CH2:6][CH:7]([C:14](=[O:20])[NH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 18357355N,N-Diisopropyl-3-cyano-3-phenylpropanamide

Product 1

HCID 18357397N,N-Diisopropyl-3-carbamoyl-3-phenylpropanamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

N,N-Diisopropyl-3-cyano-3-phenylpropanamide (21.1 g, 82 mmol) was dissolved in EtOH (130 mL) and 2 M NaOH (100 mL). Hydrogen peroxide (30%, 20.2 mL, 200 mmol) was added and the mixture was stirred at ambient temperature for two hours. The resulting precipitate was filtered, washed with water and dried, yielding the title compound as white crystals, 15.6 g (69%): 1H NMR (CDCl3) δ1.09 (d, 3H), 1.19 (d, 3H), 1.31 (m, 6H), 2.51 (dd, 1H), 3.30 (dd, 1H), 3.41 (m, 1H), 4.02 (m, 1H), 4.18 (dd, 1H), 5.7 (br, 1H), 6.4 (br, 1H), 7.21-7.42 (m, 5H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-1056e1efe18f4c79ab3264c2884f9206
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

Loading…