Formaldehyde → HCID 54698239, compound

Reaction equation

[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]([O:17][CH3:18])[C:6](=[O:16])[CH:7]=[C:8]1[C:12](=[O:13])OC(C)(C)[O:9]1.C=O.[CH3:26][NH2:27].[CH3:28]O>>[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]([O:17][CH3:18])[C:6]([C:7]1[CH2:26][N:27]([CH3:28])[C:12](=[O:13])[C:8]=1[OH:9])=[O:16]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 887Methanol

HCID 6329Methylamine

HCID 73855585N-(2-Chloro-4-fluorobenzyl)-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-acetamide

Product 1

HCID 54698239HCID 54698239, compoundYield 55%

Procedure

N-(2-Chloro-4-fluorobenzyl)-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-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 (55% yield); mp 152–155° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.11 (3H, s, NCH3), 3.75 (3H, s, OCH3), 4.17 (2H, s, NCH2), 5.01 (2H, s, NCH2), 6.99 (1H, m, aromatic), 7.15 (1H, dd, J=2.5 Hz, J=8.0 Hz, aromatic), 7.36 (1H, dd, J=5.7 Hz, J=8.8 Hz, aromatic). Anal. calcd for C14H14ClFN2O4: C, 51.15; H, 4.29; N, 8.52. Found: C, 50.62; H, 4.18; N, 8.40.