Water → 2-{4-[6-chloro-2-(1-chloro-1-methylethyl)-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate

HRID 724196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724196
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3[CH:18]=[C:19]([Cl:26])[C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:27](O)([CH3:29])[CH3:28])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].S(Cl)([Cl:33])=O.O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3[CH:18]=[C:19]([Cl:26])[C:20]([C:22]([F:24])([F:23])[F:25])=[CH:21][C:16]=3[N:15]=[C:14]2[C:27]([Cl:33])([CH3:29])[CH3:28])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 218757612-{4-[6-chloro-2-(1-hydroxy-1-methylethyl)-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate

Produkt 1

HCID 218761642-{4-[6-chloro-2-(1-chloro-1-methylethyl)-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetateAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-{4-[6-chloro-2-(1-hydroxy-1-methylethyl)-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate (300 mg, 0.68 mmol) in dichloromethane (15 ml) was added thionyl chloride (0.07 ml, 1.02 mmol) and the reaction mixture was refluxed overnight. The reaction mixture was poured into water (10 ml) and the mixture was extracted with dichloromethane (30 ml). The organic layer was washed with brine (10 ml), then dried (Na2SO4). The solvent was removed to give 273 mg (87%) of the title compound as white amorphous.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight
  2. extractionthe mixture was extracted with dichloromethane (30 ml)
  3. washThe organic layer was washed with brine (10 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-d280686afcd645f4876b00fb30e7aab6
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141580B2

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