Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methyl-(4-trifluoromethyl-benzyl)-amide
Reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH3:22])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[O:9])[C:4](=[O:23])O1.C=O.[CH3:27][NH2:28].[CH3:29]O>>[CH3:22][N:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=1)[C:8]([C:7]1[CH2:27][N:28]([CH3:29])[C:4](=[O:23])[C:5]=1[OH:6])=[O:9]Participants
4
Reactant 3
Product 1
Procedure
Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methyl-N-(4-trifluoromethylbenzyl)-acetamide (0.50 g, 1.45 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 0.31 g (64% yield) of the title compound as white crystals; mp 126–128° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 3.07 (3H, s, NCH3), 3.13 (3H, s, NCH3), 4.18 (2H, s, NCH2), 4.74 (2H, s, NCH2), 7.41 (2H, d, J=8.1 Hz, aromatics), 7.64 (2H, d, J=8.1 Hz, aromatics), 10.56 (1H, broad, OH). Anal. Calcd for C15H15F3N2O3: C, 54.88; H, 4.61; N, 8.53. Found: C, 54.93; H, 4.57; N, 8.44.
Sources & evidence
- ORD record
- ord-bac01a873a7941228ab9d9149e4c1b69
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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