HCID 21947356, compound → n-(4-Acetylamino-benzyl)-2(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamide

HRID 2214615Notes

Reaction equation

HRID 2214615 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.[C:13]([NH:16][C:17]1[CH:26]=[CH:25][C:20]([CH2:21][NH:22][O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:15])[CH3:14]>>[C:13]([NH:16][C:17]1[CH:26]=[CH:25][C:20]([CH2:21][N:22]([O:23][CH3:24])[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:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 21947356HCID 21947356, compoundHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 73855583n-(4-Acetylamino-benzyl)-2(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamideYield 92%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-(4-acetamidobenzyl)-O-methyl-hydroxylamine as described in the preparation of Compound 44-C gave the title amide as white crystals (92% yield): mp 212–215° C. (dec.) (dichloromethane-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.73 (6H, s, CH3), 2.16 (3H, s, CH3), 3.67 (3H, s, OCH3), 4.78 (2H, s, NCH2), 6.39 (1H, s, CH), 7.32 (3H, m, aromatics and NH), 7.45 (2H, m, aromatics). Anal. calcd. for C17H20N2O6: C, 57.87; H, 5.86; N, 7.94. Found: C, 57.76; H, 5.68; N, 8.51.

Sources & evidence

ORD record
ord-a85572f6a88e418a97e1b8f17ecf30a7
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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