Hydrochloric Acid → 2-{2[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-phenyl}-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole

HRID 47289

Reaktionsgleichung

Reaktionsgleichung von HRID 47289
C(S[C:4](=S)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[CH2:12][CH2:13][C:14]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])C.Cl.[NH2:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[NH2:32]>O>[Br:20][C:18]1[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([CH2:13][CH2:12][C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[NH:32][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]3[N:25]=2)[CH:19]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 438061,2-Diaminocyclohexane, trans-HCID 206283942-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester

Produkt 1

HCID 227447592-{2[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-phenyl}-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

As shown in Scheme 12, a solution of 187 mg (0.43 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester in 2.5 mL of trans-1,2 diaminocyclohexane was heated to 110° C. in a sealed pressure tube for 12 hours. The reaction mixture was diluted with water and extracted with methylene chloride twice. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (eluting with 95:5 CH2Cl2/methanol) to give a yellow oil. The oil was treated with methanolic HCl and evaporated to yield 34 mg of product as a pure hydrochloride salt.

Aufarbeitung

  1. extractionextracted with methylene chloride twice
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (eluting with 95:5 CH2Cl2/methanol)
  6. customto give a yellow oil
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cfa60ca8533b4b33a554dcc851da896b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699873B1

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