Methanol → N-[(2,4-dichlorophenyl)methyl]-1,3,3-trimethyl-5-oxoprolinamide

反応式

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N+:10]#[C-:11].[CH3:12][C:13]([CH3:20])([CH:18]=O)[CH2:14][C:15](O)=[O:16].[CH3:21][NH2:22].C[OH:24]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11](=[O:24])[C@@H:18]1[C:13]([CH3:20])([CH3:12])[CH2:14][C:15](=[O:16])[N:22]1[CH3:21]

参加物

反応物 4

HCID 887Methanol

HCID 6329Methylamine

HCID 27580712,4-Dichloro-1-(isocyanomethyl)benzene

HCID 247680973-Formyl-3-methylbutanoic acid

生成物 1

HCID 67460084N-[(2,4-dichlorophenyl)methyl]-1,3,3-trimethyl-5-oxoprolinamide

反応条件

温度: 100 °C

実験手順

To a solution of (2,4-dichlorophenyl)methyl isocyanide (0.094 g, 0.5 mmol) and 3,3-dimethyl-4-oxobutanoic acid (0.065 mg, 0.5 mmol, prepared as described below) in methanol (2 ml) was added methylamine (0.080 ml, 33% solution in ethanol). The mixture was heated to 100° C. for 30 minutes in a microwave reactor. The solvent was removed in vacuo and the residue was purified by mass-directed automated HPLC to give a colourless gum which was triturated with diethyl ether to give N-[(2,4-dichlorophenyl)methyl]-1,3,3-trimethyl-5-oxoprolinamide (0.043 g) as a sticky white solid.