5-Bromo-2-methyl-1H-benzo[d]imidazole → HCID 58107460, Verbindung

HRID 1810192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810192
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[NH:7][C:6]=2[CH:11]=1.C([Li])(C)(C)C.[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([C:22](N(OC)C)=[O:23])=[CH:20][C:19]=1[S:30](=[O:33])(=[O:32])[NH2:31]>O1CCCC1>[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([C:22]([C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[C:8]([CH3:10])[NH:7][C:6]=3[CH:11]=2)=[O:23])=[CH:20][C:19]=1[S:30]([NH2:31])(=[O:33])=[O:32]

Komponenten

5

Edukt 3

HCID 6109795-Bromo-2-methyl-1H-benzo[d]imidazoleHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 58107460HCID 58107460, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.303 g of 6-bromo-2-methyl-1H-benzoimidazole in tetrahydrofuran (20 mL) is cooled to −50° C. and treated with 2.7 mL of tert-butyllithium (1.5 M in pentane). After 2 h at −50° C. the reaction mixture is treated with 0.12 g of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide in tetrahydrofuran (10 mL). After 3 h the mixture is quenched with saturated aqueous ammonium chloride, taken up in ethyl acetate, and washed with saturated aqueous sodium chloride. The organics are dried (magnesium sulfate), concentrated and purified by silica gel chromatography (98:2 methylene chloride/methanol) to give 2-chloro-5-(2-methyl-3H-benzoimidazole-5-carbonyl)-benzenesulfonamide. MS (m/z): 348 (M−1); Rf 0.30 (9:1 methylene chloride/methanol).

Aufarbeitung

  1. customAfter 3 h the mixture is quenched with saturated aqueous ammonium chloride
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialThe organics are dried (magnesium sulfate)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (98:2 methylene chloride/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-73cba3e20b064e1fa3fc5603d7855bbf
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362063B2

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