p-Aminoacetophenone → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-(1-methoxycarbonyl-2-carbamoylethyl)urea
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=O.[N-:11]=[C:12]=[O:13].[CH3:14][O:15][C:16](=[O:23])[C@H:17]([CH2:19][C:20](=[O:22])[NH2:21])N.Cl.[NH2:25][OH:26].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:26][N:25]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:12]([NH:11][CH:17]([C:16]([O:15][CH3:14])=[O:23])[CH2:19][C:20](=[O:22])[NH2:21])=[O:13])=[CH:6][CH:5]=1)[CH3:1]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2.7 g 4-aminoacetophenone in 40 mL is THF added dropwise to a solution of 0.02 mol of asparagine methyl ester isocyanate and 5 mL pyridine in 40 mL THF, and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL CH3OH, and 0.022 mol hydroxylamine hydrochloride and 0.06 mol trimethyl orthoformate are added. The reaction mixture is heated to reflux for 10 hours. The solvent is removed by rotary evaporator. Addition of water to the residue results in precipitation of N-[4-(1-hydroxyiminoethyl)phenyl]-N'-(1-methoxycarbonyl-2-carbamoylethyl)urea, which is isolated by filtration and dried.
Workup
- customThe solvent is then removed by rotary evaporator
- additionThe residue is dispersed in 50 mL CH3OH
- temperatureThe reaction mixture is heated
- temperatureto reflux for 10 hours
- customThe solvent is removed by rotary evaporator
- additionAddition of water to the residue
Sources & evidence
- ORD record
- ord-9dafeabf17cf4a7b821cdcf6e393a8d2
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04740611
Reaction notes
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