Benzylamine → HCID 25019976, Verbindung

HRID 1259458Notizen

Reaktionsgleichung

CC1C=CC(S(O[CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCCCCCC>[CH2:26]([NH:33][CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=2[O:15][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A 200 mL round bottomed flask equipped with a magnetic stir bar is charged with [7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (40.0 g, 110 mmol) and benzylamine (35.2 g, 328 mmol). The mixture is heated to 95° C. for 3 h, and then heating is discontinued. Once the temperature of the solution is 80° C., heptane (300 mL) is added slowly, with rapid stirring. Once the suspension is cooled to rt, the solid is collected by vacuum filtration, and the filter cake is washed several times with heptane and suction dried to give the title compound (32.55 g, 100%) as a yellow powder. LCMS (Basic Method): 1.93 min, 301 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 7.77-7.70 (m, 1H), 7.47-7.18 (m, 6H), 7.10-7.06 (m, 1H), 4.47 (dd, J=2.5, 11.5 Hz, 1H), 4.37-4.29 (m, 1H), 4.15 (dd, J=7.1, 11.5 Hz, 1H), 3.73 (s, 2H), 2.43 (br s, 1H), 2.82-2.70 (m, 2H).

Aufarbeitung

customA 200 mL round bottomed flask equipped with a magnetic stir bar
temperatureheating
customis 80° C.
temperatureOnce the suspension is cooled to rt
filtrationthe solid is collected by vacuum filtration
washthe filter cake is washed several times with heptane and suction
customdried

Quellen und Nachweise

ORD-Eintrag: ord-8c6b007dcd694eedb06bee5202611242
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08466296B2

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