Benzonitrile, m-chloro- → HCID 67070903, Verbindung

HRID 732132

Reaktionsgleichung

Reaktionsgleichung von HRID 732132
[OH:1][N:2]=[C:3]([Br:5])Br.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CC(=O)OCC>[Br:5][C:3]1[N:11]=[C:10]([C:9]2[CH:12]=[CH:13][CH:14]=[C:7]([Cl:6])[CH:8]=2)[O:1][N:2]=1

Komponenten

6

Edukt 3

HCID 13015Benzonitrile, m-chloro-HCID 516892Sodium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

Produkt 1

HCID 67070903HCID 67070903, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydroxycarbonimidic dibromide (2.21 g, 10.89 mmol) was added portionwise over 1 h 20 min to a mixture of 3-chlorobenzonitrile (3.00 g, 21.29 mmol) and NaHCO3 (2.9 g, 34.87 mmol) in toluene (3 ml) at 90° C. Stirring was continued for 3 h and then the reaction mixture was cooled to r.t., diluted with EA and washed with water. The organic phase was dried and concentrated. A mixture of 3-chlorobenzonitrile and 3-bromo-5-(3-chlorophenyl)-1,2,4-oxadiazole was obtained after flash chromatography (hex/EA 10:1). 1.0 g of the mixture was dissolved in MeNH2 (4 ml, 8.5 M in EtOH) and heated in a microwave reactor for 30 min at 60° C. The volatiles were removed under reduced pressure and the residue was dissolved in water and extracted with CHCl3. The organic phase was dried and concentrated. Recrystallization from EA gave 137 mg of the title compound. 1H NMR: 3.00 (d, 3 H) 4.35 (bs, 1 H) 7.43 (t, 1 H) 7.50-7.55 (m, 1 H) 7.92 (d, 1 H) 8.03 (s, 1 H)

Aufarbeitung

  1. washwashed with water
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. additionA mixture of 3-chlorobenzonitrile

Quellen und Nachweise

ORD-Eintrag
ord-1fcec38ba4fe4e71a2b688ccd8f544c4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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