Neryl chloride → 2-[(3,7-Dimethyl-2,6(Z)-octadienyl)-thio]-1H-1,3-benzimidazole

HRID 1030576

Reaktionsgleichung

Reaktionsgleichung von HRID 1030576
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].O.[CH2:14](Cl)/[CH:15]=[C:16](\[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])/[CH3:17]>CO>[CH3:17]/[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:15]/[CH2:14][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 5874259Neryl chlorideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178527775HCID 178527775, Verbindung

Produkt 1

HCID 867457032-[(3,7-Dimethyl-2,6(Z)-octadienyl)-thio]-1H-1,3-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-mercaptobenzimidazole (5.1 g, 34 mmol) and 2N NaOH/H2O (pH 11) in methanol (100 mL) was added neryl chloride (5.85 g, 34 mmol). The reaction mixture was stirred at ambient temperature for 16 hours, evaporated in vacuo, dissolved in CH2Cl2, washed with saturated NaHCO3 and brine, and dried over Na2SO4. Evaporation of the solvent gave an oil which was flash chromatographed (Merck Kieselgel, 5% MeOH/CH2Cl2) to give the title compound which was crystallized from Et2O/pentane to give a white solid (3.4 g, 35%). m.p. 98°-101° C. NMR (CDCl3)δ7.35(m 4H) 5.25(m 2H) 4.0(d,J=6 Hz,2H), 2.05(m,4H), 1.68(s,3H), 1.62(s,3H), 1.60(s,3H).

Aufarbeitung

  1. customevaporated in vacuo
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customchromatographed (Merck Kieselgel, 5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-a55c77ed868b499299a96a94630496ec
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106863

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