Oxalyl chloride → 2-bromo-3-methoxy-N-(1-methyl-1H-tetrazol-5-yl)-4-nitrobenzamide

HRID 1754132

Reaktionsgleichung

[Br:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:16][N:17]1[C:21]([NH2:22])=[N:20][N:19]=[N:18]1.C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:3]=1[C:4]([NH:22][C:21]1[N:17]([CH3:16])[N:18]=[N:19][N:20]=1)=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

2-bromo-3-methoxy-4-nitrobenzoic acid (95 mg, 0.344 mmol) and 1-methyl-1H-tetrazol-5-amine (44 mg, 0.447 mmol) are dissolved in pyridine (6 ml). Oxalyl chloride (41 μl, 0.465 mmol) is slowly added dropwise, and the reaction mixture is subsequently warmed to 65° C. for 2 hours. The solvent is stripped off and the residue is separated by preparative HPLC. This gives 59 mg (0.165 mmol, yield 48%) of 2-bromo-3-methoxy-N-(1-methyl-1H-tetrazol-5-yl)-4-nitrobenzamide.

Aufarbeitung

customthe residue is separated by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-fc0841cc52b4490fa9318db6b0ecaaf2
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09169219B2

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