4-Nitrobenzoyl chloride → 2-(4-Nitrophenyl)Benzo[D]Thiazole

HRID 1950669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1950669
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]2[S:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 85024-Nitrobenzoyl chlorideHCID 87132-Aminothiophenol

Produkt 1

HCID 8275002-(4-Nitrophenyl)Benzo[D]ThiazoleAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 4-nitrobenzoyl chloride (1.49 g, 8.0 mmol) in benzene (anhydrous, 10 mL) was added dropwise to 2-aminothiophenol (1.0 g, 8.0 mmol in 10 ml of benzene) at room temperature. The reaction mixture was allowed to stir for 16 hr. The reaction was quenched with water (20 mL). The aqueous layer was separated and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried and evaporated. The crude product was purified with flush column, (hexane:ethyl acetate=85:15) to give 1.5 g (73.2%) of product as light yellow solid.

Aufarbeitung

  1. customThe reaction was quenched with water (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. customThe combined organic layers were dried
  5. customevaporated
  6. customThe crude product was purified
  7. customwith flush column, (hexane:ethyl acetate=85:15)

Quellen und Nachweise

ORD-Eintrag
ord-ae84bf34386f4033b27e0e6ddb894f45
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404213B2

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