Dichloromethane → 2-(2-Methoxy-4-nitrophenyl)benzothiazole

HRID 339495

Reaktionsgleichung

Reaktionsgleichung von HRID 339495
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][O:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=O.C(Cl)Cl>CCOCC>[CH3:9][O:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 87132-AminothiophenolHCID 757764-Nitro-o-anisic acid

Produkt 1

HCID 672372802-(2-Methoxy-4-nitrophenyl)benzothiazoleAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A thoroughly mixed paste of 2-aminobenzenethiol (0.63 g, 5.07 mmol) and 2-methoxy-4-nitrobenzoic acid (1.0 g, 5.07 mmol) in trimethylsilylpolyphosphate (5 ml) was stirred and heated at 150° C. under an atmosphere of argon for 1.5 h. On cooling to room temperature the reaction mixture was a solid mass to which was added DCM (35 ml) and Et2O (50 ml). The solid was broken up and collected by filtration, then recrystallised from AcOH and dried under high vacuum for 18 h to give the title compound (0.90 g, 62%) as a yellow solid.

Aufarbeitung

  1. temperatureOn cooling to room temperature the reaction mixture
  2. filtrationcollected by filtration
  3. customrecrystallised from AcOH
  4. customdried under high vacuum for 18 h

Quellen und Nachweise

ORD-Eintrag
ord-a24f807588bb43c18473164e23930830
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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