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

HRID 62816

Reaktionsgleichung

Reaktionsgleichung von HRID 62816
[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-7d115dd033a8422f9a090d4e1b705403
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447033B2

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