Formaldehyde → HCID 54698240, compound

HRID 2214639Notes

Reaction equation

HRID 2214639 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

5

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 6329MethylamineHCID 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.

Sources & evidence

ORD record
ord-5a015c6a8a9549a488ec53dae6538de9
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

Loading…