Sodium hydride → 2-(1H-benzimidazol-2-yl-thiomethyl)-benzothiazole

HRID 414714

Reaktionsgleichung

Reaktionsgleichung von HRID 414714
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]=1[SH:12].Cl[CH2:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1>CN(C)C=O>[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][CH2:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3049782-(Chloromethyl)benzothiazoleHCID 178527775HCID 178527775, Verbindung

Produkt 1

HCID 6779102-(1H-benzimidazol-2-yl-thiomethyl)-benzothiazoleAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.5 g (50 mmol-80%) of sodium hydride were added under nitrogen to a stirred solution of 7.6 g (50 mmol) of 2-benzimidazolethiol in 76 ml of dimethylformamide and after one hour, 7.2 g (40 mmol) of 2-chloromethyl-benzothiazole were added with ice cooling. The mixture stood at room temperature for 2 hours and the solution was concentrated under reduced pressure in a nitrogen stream. The residue was dissolved in ethyl acetate and the solution was washed with ice cold 2N sodium hydroxide solution and aqueous saturated sodium chloride solution, was dried over magnesium sulfate and evaporated to dryness under reduced pressure to obtain 6.91 g (58% yield) of 2-(1H-benzimidazol-2-yl-thiomethyl)-benzothiazole in the form of pale yellow crystals after crystallization from dichloromethane melting at 159°-162° C.

Aufarbeitung

  1. concentrationthe solution was concentrated under reduced pressure in a nitrogen stream
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with ice cold 2N sodium hydroxide solution and aqueous saturated sodium chloride solution
  4. dry with materialwas dried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dea7ee09863c4df48351fbfb2ec8d320
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04794122

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