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Triethylamine → 2-(4-Chloro-phenyl)-1-(4-methanesulfonyl-phenyl)-1H-imidazole-4-carbaldehyde

HRID 1166391
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1166391
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C>ClCCl.CS(C)=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:23][CH:22]=3)[CH:16]=[C:17]([CH:19]=[O:20])[N:18]=2)=[CH:10][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 108325102-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-methanol

Produkt 1

HCID 117929022-(4-Chloro-phenyl)-1-(4-methanesulfonyl-phenyl)-1H-imidazole-4-carbaldehydeAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 8 ml of a 1:1 mixture of dimethyl sulfoxide and dichloromethane stirring in a dry ice/isopropanol bath under nitrogen was added dropwise oxalyl chloride (321 μl, 3.69 mmol) After stirring for 10 minutes, a solution of 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-methanol (Example 158) (670 mg, 1.85 mmol) in 25 ml of a 1:1 mixture of dimethyl sulfoxide and dichloromethane. Stirring was continued while warming to 0° C., where it was maintained for 15 minutes. Triethylamine (1.87 g, 18.5 mmol) was added, and the mixture was stirred overnight while warming to room temperature. The mixture was partitioned between dichloromethane and water, the organic layer was washed with water and then brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane gave the title compound as an off-white solid (330 mg): mp (DSC) 203° C. Anal. Calc'd. for C17H13ClN2O3S (MW 360.82): C, 56.59; H, 3.63; N, 7.76. Found: C, 56.24; H, 3.62; N, 7.50.

Aufarbeitung

  1. stirringStirring
  2. temperaturewhere it was maintained for 15 minutes
  3. stirringthe mixture was stirred overnight
  4. temperaturewhile warming to room temperature
  5. customThe mixture was partitioned between dichloromethane and water
  6. washthe organic layer was washed with water
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c1d91e67459144b5ae3ca1ad602e49c1
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06613789B2

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