(Diethylamino)sulfur trifluoride → HCID 59699468, Verbindung

HRID 901083Notizen

Reaktionsgleichung

[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=O)=[CH:10][CH:9]=2)[O:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4]1.C(N(S(F)(F)[F:29])CC)C>ClCCl>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:16][F:29])=[CH:10][CH:9]=2)[O:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4]1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

To a solution of 20 (390.9 g, 1.11 mol) and SbCl3 (7.62 g, 0.0334 mol) in anhydrous dichloromethane (2.27 L) at −15° C., diethylamino sulfurtrifluoride (DAST) (258 ml, 2.0 mol) was added drop-wise. The reaction mixture was stirred for 3 hours at −20° C. and then allowed to warm up to room temperature overnight. The reaction was quenched with 1N NaOH solution until pH=3-4 at −20° C., and then solid NaHCO3 was added to pH=8. The organic layer was separated and the aqueous solution was extracted with dichloromethane. The combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated to provide 330 g of the desired product as a brown oil.

Aufarbeitung

temperatureto warm up to room temperature overnight
customThe reaction was quenched with 1N NaOH solution until pH=3-4 at −20° C.
additionsolid NaHCO3 was added to pH=8
customThe organic layer was separated
extractionthe aqueous solution was extracted with dichloromethane
washThe combined organic extracts were washed with water, brine
dry with materialdried over Na2SO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-67be831b45aa455f810b4e65e57d149c
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07361689B2

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