HCID 21947412, compound → HCID 73855545, compound

HRID 1836486Notes

Reaction equation

HRID 1836486 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.[F:13][C:14]1[CH:26]=[CH:25][C:17]([CH2:18][NH:19][O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:16][CH:15]=1>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:19]([CH2:18][C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:26][CH:25]=2)[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 21947412HCID 21947412, compoundHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 73855545HCID 73855545, compoundYield 91%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-(4-fluorobenzyl)-O-isobutyl-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (91% yield): mp 105-106° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 0.98 (3H, d, J=6.45 Hz, CH3), 1.77 (6H, s, CH3), 1.95 (1H, m, CH), 3.64 (2H, d, J=6.63 Hz, OCH2), 4.80 (2H, s, NCH2), 6.41 (1H, s, CH), 7.03 (2H, m, aromatics), 7.36 (2H, m, aromatics). Anal. calcd for C18H22FNO5: C, 61.53; H, 6.31; H, 3.98. Found: C, 61.47; H, 6.39; N, 3.97.

Sources & evidence

ORD record
ord-323d61dde95a4a209ac55afff177f8d1
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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