Pyridine → 2-[(5-Nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate

HRID 731767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731767
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][OH:13])=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.N1C=CC=CC=1>ClCCl>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:13][CH2:12][CH2:11][S:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)=[O:20])=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 433853802-[(5-Nitro-2-pyridinyl)thio]ethanol

Produkt 1

HCID 114938062-[(5-Nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A homogeneous mixture of 2-[(5-nitro-2-pyridinyl)thio]ethanol (7) (45 mg, 0.22 mmol), 4-chlorobenzoyl chloride (33 μL, 0.26 mmol) and pyridine (45 μL, 0.56 mmol) in anhydrous dichloromethane (1.5 mL) was stirred at room temperature for 48 h. The reaction mixture was quenched with 1N HCl and the organic phase was washed with saturated aqueous solution of NaHCO3, brine and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate (8). LCMS: purity: 90%; MS (m/e): 340 (M+)

Aufarbeitung

  1. customThe reaction mixture was quenched with 1N HCl
  2. washthe organic phase was washed with saturated aqueous solution of NaHCO3, brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9bbe25831e9c45c39f003ee4b950b899
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585883B2

Notizen zur Reaktion

Wird geladen…