2-Bromobenzoic acid → 2-bromo-N-(4-nitrophenyl)benzamide

HRID 487411

Reaktionsgleichung

S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([O-:17])=[O:16]>C1(C)C=CC=CC=1.CN(C)C=O.CN1C(=O)CCC1>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1)=[O:10]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and N, N-dimethylformamide (DMF) (5 ml) and the mixture heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and NMP (120 ml), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours when a solid precipitated. Water (360 ml) was added with rigorous stirring and the suspended solid collected by filtration, and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide (B) as a solid, in 87% yield; m.p. 200°-202° C.; NMR(d6 -DMSO): 7.4-7.8(m, 7H), 8.0(d, 2H), 8.3(d, 2H), 11.5(brs, 1H); which was used without further purification.

Aufarbeitung

temperatureThe solution was cooled to 20° C.
temperaturemaintaining the temperature of the reaction mixture between 20°-25° C
customprecipitated
additionWater (360 ml) was added
stirringwith rigorous stirring
filtrationthe suspended solid collected by filtration
washwashed successively with water, toluene and acetonitrile

Quellen und Nachweise

ORD-Eintrag: ord-9a0bfd21d74c463aa22299849bce18a8
Quelldatensatz: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05294716

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