Sodium Carbonate → HCID 11610203, Verbindung

HRID 2198784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2198784
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[CH2:18]([SH:21])[CH2:19][SH:20].C(=O)([O-])[O-].[Na+].[Na+]>CS(O)(=O)=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:11][N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[S:21][CH2:18][CH2:19][S:20]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 109021,2-EthanedithiolHCID 110103354-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-one

Produkt 1

HCID 11610203HCID 11610203, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

A solution 1-[4-(4-chlorophenyl)butan-2-on-1-yl]imidazole (2.49 g) in 98% methanesulfonic acid (10 ml) was treated with ethane-1,2-dithiol (6 ml) and the mixture stirred overnight at room temperature. The resulting mixture was poured into excess aqueous sodium carbonate, extracted with ether (3×20 ml), the extracts washed, dried (MgSO4) and the ether evaporated. The residue was taken up in a small volume of ether and treated with ethereal hydrogen chloride until precipitation was complete. The resulting precipitate was filtered off and recrystallized from methanol/ethyl acetate, to give 1-[[2-(2-(4-chlorophenyl)ethyl)-1,3-dithiolan-2-yl]methyl]imidazole hydrochloride, m.p. 206.5°-208° C. Similarly proceeding as above, but substituting the appropriate ethan-1,2-dithiol and the appropriate ketone as exemplified in Preparations 1, 2, 3 or 4 in place of 1-[4-(4-chlorophenyl)butan-2-on-1-yl]imidazole there may be prepared, for example, the following compounds:

Aufarbeitung

  1. extractionextracted with ether (3×20 ml)
  2. washthe extracts washed
  3. dry with materialdried (MgSO4)
  4. customthe ether evaporated
  5. additiontreated with ethereal hydrogen chloride until precipitation
  6. filtrationThe resulting precipitate was filtered off
  7. customrecrystallized from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5da86096e18c4925afdbbf2613ed84f8
Quelldatensatz
uspto-grants-1982_11
Patentnummer
US04359475

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