n-[3-(3,4-Dichlorophenyl)-propyl]-o-methyl-hydroxylamine → n-[3-(3,4-Dichloro-phenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamide

HRID 1836543Notes

Reaction equation

HRID 1836543 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.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][NH:24][O:25][CH3:26])[CH:17]=[CH:18][C:19]=1[Cl:20]>>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][N:24]([O:25][CH3:26])[C:8](=[O:9])[CH:7]=[C:5]2[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]2)[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

3

Reactant 2

HCID 23499566n-[3-(3,4-Dichlorophenyl)-propyl]-o-methyl-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 73855586n-[3-(3,4-Dichloro-phenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamideYield 95%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-[3-(3,4-dichlorophenyl)-propyl]-O-methyl-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (95% yield): mp 105-106° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.91 (6H, s, CH3), 2.13 (2H, m, CH2), 2.77 (2H, t, J=7.9 Hz, CH2), 3.86 (2H, t, J=7.0 Hz, NCH2), 3.88 (3H, s, OCH3), 6.54 (1H, broad s, CH), 7.2 (H, broad dd, aromatic), 7.44 (1H, broad d, J=2 Hz, aromatic), 7.50 (1H, d, J=8.1 Hz, aromatic). Anal. calcd for C17H19Cl2NO5: C, 52.59; H, 4.93; N, 3.61. Found: C, 52.68; H, 5.08; N, 3.50.

Sources & evidence

ORD record
ord-33bcb4290d0c42189ee12b0a9fb790fb
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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