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

HRID 1836524Notes

Reaction equation

HRID 1836524 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.[CH3:13][O:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:15]([O:14][CH3:13])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 23499567o-Methyl-n-(4-trifluoromethyl-benzyl)-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555482-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methoxy-n-(4-trifluoromethylbenzyl)-acetamideYield 97%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with O-methyl-N-(4-trifluoromethyl-benzyl)-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (97% yield): mp 110° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.76 (6H, s, CH3), 3.71 (3H, s, OCH3), 4.87 (2H, s, NCH2), 6.40 (1H, s, CH), 7.47 (2H, m, aromatics), 7.59 (2H, m, aromatics). Anal. calcd for C16H16F3NO5: C, 53.49; H, 4.49; N, 3.90. Found: C, 53.48; H, 4.53; N, 3.83.

Sources & evidence

ORD record
ord-73564fc522124135baff78df4458efe1
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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