Methanesulfonyl chloride → N'-t-butyl-N-(5-bromonicotinoyl)-N'-(4-chlorobenzoyl)hydrazine

HRID 21650

Reaktionsgleichung

[C:1]([N:5]([C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[NH2:6])([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:25]=1)[C:22](O)=[O:23].CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:1]([N:5]([C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)[NH:6][C:22](=[O:23])[C:21]1[CH:25]=[C:17]([Br:16])[CH:18]=[N:19][CH:20]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 23 °C

Versuchsvorschrift

A solution of N'-t-butyl-N'-(4-chlorobenzoyl)hydrazine (0.5 g, 0.0022 mol) and 5-bromonicotinic acid (0.44 g, 0.0022 mol) in 10 ml of methylene chloride containing triethylamine (0.33 g) was added to a solution of methanesulfonyl chloride (0.25 g, 0.0022 mol) in 10 ml of methylene chloride at 0° C. The resulting mixture was stirred at 23° C. for 2 hours and then was allowed to stand overnight at 23° C. Aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was re-extracted with methylene chloride. The organic extracts were evaporated to give a yellow solid which was triturated with hexane/methylene chloride to afford N'-t-butyl-N-(5-bromonicotinoyl)-N'-(4-chlorobenzoyl)hydrazine as an off-white solid: m.p. 193°-197° C.

Aufarbeitung

waitto stand overnight at 23° C
customthe layers were separated
extractionThe aqueous layer was re-extracted with methylene chloride
customThe organic extracts were evaporated
customto give a yellow solid which
customwas triturated with hexane/methylene chloride

Quellen und Nachweise

ORD-Eintrag: ord-da667ad184574d05aef190feca4c039a
Quelldatensatz: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05424333

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