tert-Butyl-3-aminobenzoate → 3-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl ester

HRID 1518990

Reaktionsgleichung

Reaktionsgleichung von HRID 1518990
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:16]=1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][S:21]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)(=[O:23])=[O:22])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 2737408tert-Butyl-3-aminobenzoateHCID 3164136Pyridine-3-sulfonyl chloride

Produkt 1

HCID 673108723-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl esterAusbeute 104,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl-3-aminobenzoate (100 mg, 0.5 mmol) and pyridine-3-sulfonylchloride (110 mg, 0.5 mmol) in pyridine (5 ml) was heated to 50° C. for 90 min. On cooling, the reaction was diluted with toluene (100 ml) and concentrated in vacuo. This was repeated with further aliquots of toluene until all the pyridine had been removed to afford the title compound as a yellow oil (175 mg). HPLC retention time 4.27 min. Mass spectrum (ES+) m/z 335 (M+H).

Aufarbeitung

  1. temperatureOn cooling
  2. concentrationconcentrated in vacuo
  3. customhad been removed

Quellen und Nachweise

ORD-Eintrag
ord-40ae53a1b80a44a7baa4fc46a4936895
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073834B2

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