Sodium Carbonate → 3-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxide

HRID 628012

Reaktionsgleichung

Reaktionsgleichung von HRID 628012
ClC1C=CC=C(C(OO)=[O:9])C=1.[I:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][C:22]1[CH:26]=[CH:25][S:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[I:12][C:13]1[CH:14]=[N+:15]([O-:9])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][C:22]1[CH:26]=[CH:25][S:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 579002113-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine

Produkt 1

HCID 582840413-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxideAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

m-Chloroperbenzoic acid (1.55 g, 6.29 mmol) was added portionwise to a solution of 1.0 g (3.02 mmol) of 3-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine in 150 ml of methylene chloride. The mixture was stirred for 18 hours then mixed with 100 ml of 1 M aqueous sodium carbonate. The organic layer was separated and the aqueous one was extracted 2 times with 10 ml of methylene chloride. Combined organic extracts were washed with brine and dried over sodium sulfate. The solution was concentrated in vacuum to give 3-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxide (1.01 g, 92%). MS: (ESI+) 348.0

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous one was extracted 2 times with 10 ml of methylene chloride
  3. washCombined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solution was concentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bb7485e41aca4e91974363d6d971d27c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309265B2

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