Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (4-fluoro-2-trifluoromethyl-benzyl)-methoxy-amide

HRID 2214719Notes

Reaction equation

HRID 2214719 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]([F:24])([F:23])[F:22])[O:11][CH3:12])=[O:9])[C:4](=[O:25])O1.C=O.[CH3:29][NH2:30].[CH3:31]O>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8]([C:7]2[CH2:29][N:30]([CH3:31])[C:4](=[O:25])[C:5]=2[OH:6])=[O:9])=[C:15]([C:21]([F:22])([F:23])[F:24])[CH:16]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 22018472Paraformaldehyde methylamineHCID 738555752-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluoro-2-trifluoromethyl-benzyl)-n-methoxy-acetamide

Product 1

HCID 547046904-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (4-fluoro-2-trifluoromethyl-benzyl)-methoxy-amideYield 42%

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-(4-fluoro-2-trifluoromethylbenzyl)-N-methoxy-acetamide (0.14 g, 0.37 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 0.056 g (42% yield) of the title compound as white crystals; mp 167° C. (dec) (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 3.13 (3H, s, NCH3), 3.71 (3H, s, OCH3), 4.21 (2H, s, NCH2), 5.09 (2H, s, NCH2), 7.22–7.27 (1H, m, aromatic), 7.39–7.46 (2H, m, aromatics). Anal. Calcd for C15H14F4N2O4: C, 49.73; H, 3.89; N, 7.73. Found: C, 49.74; H, 3.92; N, 7.70.

Sources & evidence

ORD record
ord-fc19227d5c174a968b0aedbd87c11d41
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

Loading…