n-(4-Fluoro-2-trifluoromethyl-benzyl)-o-methyl-hydroxylamine → 2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluoro-2-trifluoromethyl-benzyl)-n-methoxy-acetamide

HRID 1836527Notes

Reaction equation

HRID 1836527 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.[F:13][C:14]1[CH:23]=[CH:22][C:17]([CH2:18][NH:19][O:20][CH3:21])=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:19]([CH2:18][C:17]2[CH:22]=[CH:23][C:14]([F:13])=[CH:15][C:16]=2[C:24]([F:27])([F:25])[F:26])[O:20][CH3:21])=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 23499553n-(4-Fluoro-2-trifluoromethyl-benzyl)-o-methyl-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555752-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluoro-2-trifluoromethyl-benzyl)-n-methoxy-acetamideYield 98%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-(4-fluoro-2-trifluoromethyl-benzyl)-O-methyl-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (98% yield): mp 129-130° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.76 (6H, s, CH3), 3.69 (3H, s, OCH3), 5.04 (2H, s, NCH2), 6.45 (1H, s, CH), 7.21 (1H, m, aromatic), 7.37 (1H, m, aromatic), 7.47 (1H, m, aromatic). Anal. calcd for C16H15F4NO5: C, 50.94; H, 4.01; N, 3.71. Found: C ,50.96; H, 4.07; N, 3.66.

Sources & evidence

ORD record
ord-3b5942e238cb441da7698de024fe83d0
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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