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

HRID 2181120Notes

Reaction equation

HRID 2181120 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.[CH:13]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[CH2:19][NH:20][O:21][CH3:22])([CH3:15])[CH3:14]>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:20]([CH2:19][C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[O:16][CH:13]([CH3:15])[CH3:14])[O:21][CH3:22])=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 22485629n-(2-Isopropoxy-benzyl)-o-methyl-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555562-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(2-isopropoxybenzyl)-n-methoxy-acetamideYield 93%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-(2-isopropoxy-benzyl)-O-methyl-hydroxylamine as described in the preparation of compound 1-C gave the title amide as white crystals (93% yield): mp 103° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.34 (6H, d, J=6.0 Hz, CH3), 1.75 (6H, s, CH3), 3.68 (3H, s, OCH3), 4.60 (1H, m, CH), 4.95 (2H, broad s, NCH2), 6.44 (1H, s, CH), 6.89 (2H, m, aromatics), 7.2-7.3 (2H, m, aromatics). Anal. calcd for C18H23NO6: C, 61.88; H, 6.64; N, 4.01. Found: C, 61.22; H, 6.33; N, 3.87.

Sources & evidence

ORD record
ord-b20012f119cb4ac5924d08b7da62edb4
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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