HCID 12146891, compound → HCID 87937840, compound

HRID 1836483Notes

Reaction equation

HRID 1836483 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.[CH2:13]([O:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:14]>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:16]([O:15][CH2:13][CH3:14])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 12146891HCID 12146891, compoundHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 87937840HCID 87937840, compoundYield 92%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with O-ethyl-N-4-fluorobenzyl-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (92% yield): mp 95-96° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.27 (3H, t, J=7.07 Hz, CH3), 1.77 (6H, s, CH3), 3.90 (2H, q, J=7.07 Hz, OCH2), 4.81 (2H, s, NCH2), 6.41 (1H, s, CH), 7.03 (2H, m, aromatics), 7.37 (2H, m, aromatics). Anal. calcd for C16H18FNO5: C, 59.43; H, 5.61; N, 4.33. Found: C, 59.50; H, 5.60; N, 4.17.

Sources & evidence

ORD record
ord-cc44666fc6eb4b3d83339556c8af2aa0
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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