Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-methoxy-amide

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]([O:24][CH3:25])[C:13](=[O:23])[CH:14]=[C:15]2[C:19](=[O:20])OC(C)(C)[O:16]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C=O.[CH3:28][NH2:29].[CH3:30]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]([O:24][CH3:25])[C:13]([C:14]2[CH2:28][N:29]([CH3:30])[C:19](=[O:20])[C:15]=2[OH:16])=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

Edukt 3

HCID 887Methanol

HCID 22018472Paraformaldehyde methylamine

HCID 73855586n-[3-(3,4-Dichloro-phenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamide

Produkt 1

HCID 547046254-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-methoxy-amideAusbeute 58 %

Versuchsvorschrift

Reaction of N-[3-(3,4-dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-acetamide (0.480 g, 1.16 mmol) with the paraformaldehyde-methylamine adduct in methanol using a procedure similar to the one described in the preparation of compound 44 (method 44B) gave 0.250 g (58% yield) of the title compound as white crystals; mp 106–108° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 2.01 (2H, m, CH2), 2.65 (2H, t, J=7.6 Hz, CH2), 3.14 (3H, s, NCH3), 3.73 (3H, s, OCH3), 3.77 (2H, t, J=7.0 Hz, NCH2), 4.11 (2H, s, NCH2), 7.04 (1H, dd, J=2.0 Hz and J=8.1 Hz, aromatic), 7.30 (1H, d, J=2.0 Hz, aromatic), 7.36 (1H, d, J=8.1 Hz, aromatic), 11.67 (1H, broad s, OH). Anal. Calcd for C16H18Cl2N2O4: C, 51.49; H, 4.86; N, 7.51. Found: C, 51.65; H, 4.90; N, 7.45.