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4-Toluenesulfonyl chloride → 1-((4-Methylphenyl)sulfonyl)-1H-imidazole-4-carboxaldehyde

HRID 922705
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922705
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)=[O:2].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(N(CC)CC)C.CCCCCCC>CN(C)C(=O)C.O>[S:14]([N:6]1[CH:7]=[C:3]([CH:1]=[O:2])[N:4]=[CH:5]1)([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8900HeptaneHCID 764281H-Imidazole-4-carbaldehyde

Produkt 1

HCID 117157721-((4-Methylphenyl)sulfonyl)-1H-imidazole-4-carboxaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

4-Formylimidazole (20.0 g, 208.14 mmol) and p-toluenesulfonyl chloride (43.7 g, 229.0 mmol) were suspended in N,N-dimethylacetamide (200 mL). To the obtained suspension was added dropwise triethylamine (23.2 g, 229.0 mmol) at 10° C. or below, and the mixture was stirred at 10° C. or below for 1 hr or more. To the reaction mixture was added n-heptane (60 mL) at 30° C. or below. To the obtained solution was added dropwise water (240 mL) at 30° C. or below for crystallization. The mixture was stirred at room temperature for 1 hr or more to give crystals. The obtained crystals were collected by filtration, and washed with water (300 mL) to give wet crystals. The obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C. to give 1-tosyl-4-formyl-1H-imidazole (44.2 g, 176.6 mmol). yield 85%.

Aufarbeitung

  1. customfor crystallization
  2. stirringThe mixture was stirred at room temperature for 1 hr or more
  3. customto give crystals
  4. filtrationThe obtained crystals were collected by filtration
  5. washwashed with water (300 mL)
  6. customto give wet crystals
  7. customThe obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-55cc73cf521149e091891a97668c18b0
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278938B2

Notizen zur Reaktion

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