HCID 23499563, compound → HCID 74057333, compound

HRID 1836547Notes

Reaction equation

HRID 1836547 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][N:14]([CH3:27])[CH2:15][CH2:16][O:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1>>[CH3:13][N:14]([CH3:27])[CH2:15][CH2:16][O:17][N:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:8](=[O:9])[CH:7]=[C:5]1[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]1

Participants

3

Reactant 2

HCID 23499563HCID 23499563, compoundHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 74057333HCID 74057333, compoundYield 30%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with O-(2-dimethylamino-ethyl)-N-(4-fluorobenzyl)-hydroxylamine as described in the preparation of compound 1-A gave the title amide as white crystals (30% yield): mp 95-96° C. (ether-hexane). 1HNMR 400 MHz (DMSO-d6) δ (ppm): 1.70 (6H, s, CH3), 2.16 (6H, s, NCH3), 2.44 (2H, t, J=5.3 Hz, CH2), 3.97 (2H, t, J=5.3 Hz, CH2), 4.79 (2H, s, NCH2), 6.52 (1H, s, CH), 7.18 (2H, m, aromatics), 7.34 (2H, m, aromatics). Anal. calcd for C18H23FN2O5: C, 59.00; H, 6.32; N, 7.64. Found: C, 58.73; H, 6.13; N, 7.40.

Sources & evidence

ORD record
ord-eba3dc1631b44ee5b043d9e2bd5c5cf9
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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