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

HRID 1836515Notes

Reaction equation

HRID 1836515 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][C:14]1[CH:23]=[CH:22][C:17]([CH2:18][NH:19][O:20][CH3:21])=[CH:16][CH:15]=1>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:19]([O:20][CH3:21])[CH2:18][C:17]2[CH:22]=[CH:23][C:14]([CH3:13])=[CH:15][CH:16]=2)=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 23499551n-(4-Methylbenzyl)-o-methyl-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555682-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methoxy-n-(4-methylbenzyl)-acetamideYield 78%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-(4-methylbenzyl)-O-methyl-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (78% yield): mp 108-110° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.92 (6H, s, CH3), 2.5 (3H, s, CH3), 3.84 (3H, s, OCH3), 4.97 (2H, s, NCH2), 6.57 (1H, s, CH), 7.31 (2H, d, J=8.1 Hz, aromatics), 7.42 (2H, d, J=8.1 Hz, aromatics). Anal. calcd for C16H19NO5: C, 62.94; H, 6.27; N, 4.59. Found: C, 63.14; H, 5.93; N, 4.34.

Sources & evidence

ORD record
ord-22d4462707224962968356ed44fbdf8b
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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