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Thionyl Chloride → 3-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole

HRID 617630
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 617630
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][C:15]1[N:16]=[CH:17][N:18]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=1)[N:7]=[C:6]2[CH2:39]O.S(Cl)([Cl:43])=O.C(Cl)(Cl)Cl.C(O)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:43][CH2:39][C:6]1[C:5]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:8]([CH2:14][C:15]2[N:16]=[CH:17][N:18]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=2)[N:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 154286385,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-methanolHCID 21889567Chloroform ethanol

Produkt 1

HCID 154286393-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-methanol (180.0 g) was ground into a powder form using a mortar and suspended in dichloromethane (1,700 ml) at room temperature. After suspension, the reaction solution was stirred with cooling in an ice bath. To this was added dropwise 48.6 ml of thionyl chloride spending 5 minutes. It was observed 1 minute thereafter that the spot of the material almost disappeared on a thin layer chromatography (chloroform/ethanol=30/1). The reaction solution was poured into saturated sodium bicarbonate aqueous solution (2,000 ml) and extracted with chloroform (5,000 ml), and the extract was dried with sodium sulfate, filtered and then evaporated under a reduced pressure to obtain colorless solid (165.1 g). This solid substance was used in the subsequent reaction as such.

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. extractionextracted with chloroform (5,000 ml)
  3. dry with materialthe extract was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-01fda1a5764a4ddc9b03174ac6869a51
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05948913

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