2-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate → 2-[(5-Nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate

HRID 731769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731769
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][O:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].ClC1C=CC=C(C(O[O-])=[O:31])C=1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH2:11][CH2:12][O:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[O:31])=[N:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 116242282-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate2×HCID 14904487m-Chloroperbenzoate

Produkt 1

HCID 115304832-[(5-Nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-(5-nitro-2-pyridinylthio)ethyl-3-chlorobenzoate, (5) [20 mg, 0.059 mmol; prepared according to the method outlined in Scheme 2; 1H NMR (CDCl3): δ 9.22 (d, J=1.8 Hz, 1H), 8.24 (dd, J=2.4 and 9.0 Hz, 1H), 7.95-7.91 (m, 1H), 7.90 (t, J=0.9 Hz, 1H), 7.56-7.51 (m, 1H), 7.39 (d, J=8.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 4.61 (t, J=6.6 Hz, 2H), 3.68 (t, J=6.6 Hz, 2H)] and m-chloroperbenzoate (m-CPBA) 50%, 21 mg, 0.060 mmol) was stirred at room temperature for 1.25 h. The reaction mixture was then diluted with dichloromethane and washed with saturated aqueous solution of NaHCO3 and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)sulfinyl]ethyl-3-chlorobenzoate (6). LCMS: purity: 99%; MS (m/e): 355 (MH+).

Aufarbeitung

  1. customprepared
  2. washwashed with saturated aqueous solution of NaHCO3
  3. dry with materialdried over anhydrous MgSO4
  4. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7279e71db49340c7a70aa4f101ea9ab4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585883B2

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