Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methoxy-(4-trifluoromethyl-benzyl)-amide
Reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([O:22][CH3:23])[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:24])O1.C=O.[CH3:28][NH2:29].[CH3:30]O>>[CH3:23][O: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[CH2:28][N:29]([CH3:30])[C:4](=[O:24])[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-methoxy-N-(4-trifluoromethylbenzyl)-acetamide (0.20 g, 0.56 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 0.10 g (52% yield) of the title compound as white crystals; mp 145° C. (dec) (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 3.11 (3H, s, NCH3), 3.75 (3H, s, OCH3), 4.17 (2H, s, NCH2), 4.94 (2H, s, NCH2), 7.45 (2H, d, J=8.1 Hz, aromatics), 7.61 (2H, d, J=8.1 Hz, aromatics). Anal. Calcd for C15H15F3N2O4: C, 52.33; H, 4.39; N, 8.13. Found: C, 52.17; H, 4.34; N, 7.98.
Sources & evidence
- ORD record
- ord-1e380a66c43047ec889ce884737d4866
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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