Formaldehyde → HCID 54698240, compound

Reaction equation

[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

Participants

Reactant 4

HCID 712Formaldehyde

HCID 887Methanol

HCID 6329Methylamine

HCID 69655535HCID 69655535, compound

Product 1

HCID 54698240HCID 54698240, compoundYield 56%

Procedure

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.