Formaldehyde → HCID 54698240, Verbindung

Reaktionsgleichung

[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][CH:7]([N:16]([CH3:28])[C:17](=[O:27])[CH:18]=[C:19]2[C:23](=O)[O:22]C(C)(C)[O:20]2)[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C=O.[CH3:33][NH2:34].[CH3:35]O>>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:7]([N:16]([CH3:28])[C:17]([C:18]2[CH2:33][N:34]([CH3:35])[C:23](=[O:22])[C:19]=2[OH:20])=[O:27])[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:30][CH:29]=2)=[CH:14][CH:13]=1

Komponenten

Edukt 4

HCID 712Formaldehyde

HCID 887Methanol

HCID 6329Methylamine

HCID 69655535HCID 69655535, Verbindung

Produkt 1

HCID 54698240HCID 54698240, VerbindungAusbeute 56 %

Versuchsvorschrift

N-[1-(4-Chloro-benzyl)-2-(4-chloro-phenyl)-ethyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide, prepared using the methods described in the previous examples, was treated in methanol with paraformaldehyde and methylamine as described in the preparation of Compound 44, Method 44B, to give the title compound as white crystals (56% yield); mp 152–154° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm): mixture of rotamers: 2.7–3.0 (4H, m, CH2), 2.84 (3H, s, NCH3), 2.9 (3H, broad s, NCH3), 3.4 and 3.7 (2H, two broad s, NCH2), 4.16 and 4.9 (1H, broad m, CH), 7.15–7.34 (8H, m, aromatics), 10.7 and 11.0 (1H, two s, OH). HRMS (MAB N2) calculated for C22H22Cl2N2O3: [M]+: 432.100748. found: 432.100835.