p-Toluenesulfonic acid → 6-Methoxy-2-(4-nitrophenyl) benzothiazole

HRID 339492

Reaktionsgleichung

Reaktionsgleichung von HRID 339492
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[SH:10].[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18]2[S:10][C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 85024-Nitrobenzoyl chlorideHCID 2355092-Amino-5-methoxybenzene-1-thiol

Produkt 1

HCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazoleAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-methoxybenzenethiol (5.0 g, 32.2 mmol) and 4-nitrobenzoyl chloride (6.0 g, 32.2 mmol) in toluene (250 ml) was heated under reflux with a catalytic amount of 4-toluenesulphonic acid in a Dean-Stark trap for 6 h. On cooling to room temperature the precipitate was collected by filtration, washed with toluene and recrystallised from AcOH to give the title compound (7.0 g, 76%) as a pale yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. filtrationwas collected by filtration
  3. washwashed with toluene
  4. customrecrystallised from AcOH

Quellen und Nachweise

ORD-Eintrag
ord-848e7a26756a46558dcb5d9f1baf8bc7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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