p-Toluenesulfonic acid → 5-chloro-2-cyclohexyl-1H-benzimidazole-1-propanol

HRID 258842

Reaktionsgleichung

Reaktionsgleichung von HRID 258842
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13].[CH3:14][C:15]1[CH:20]=[CH:19][C:18](S(O)(=O)=O)=[CH:17][CH:16]=1.C1(C=O)CCCCC1>O.CC1C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:1][C:2]=2[CH:7]=1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 16275CyclohexanecarboxaldehydeHCID 30173573-((2-Amino-4-chlorophenyl)amino)propan-1-ol

Produkt 1

HCID 131056175-chloro-2-cyclohexyl-1H-benzimidazole-1-propanolAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a stirred and refluxing (water-separator) mixture of 30 parts of 3-[(2-amino-4-chlorophenyl)amino]-1-propanol and 0.1 parts of 4-methylbenzenesulfonic acid in 405 parts of methylbenzene is added dropwise a solution of 34 parts of cyclohexanecarboxaldehyde in 45 parts of methylbenzene. Upon completion, stirring is continued for 1 hour at reflux temperature with water-separator. The methylbenzene is removed by evaporation in vacuo and the residue is triturated in 2,2'-oxybispropane. The product is filtered off and dried, yielding 16.5 parts (38%) of 5-chloro-2-cyclohexyl-1H-benzimidazole-1-propanol; mp. 95° C.

Aufarbeitung

  1. temperaturerefluxing
  2. stirringUpon completion, stirring
  3. customThe methylbenzene is removed by evaporation in vacuo
  4. customthe residue is triturated in 2,2'-oxybispropane
  5. filtrationThe product is filtered off
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cfbd8305b5374951bdde0daa251abbdb
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04035369

Verknüpfte Notizen

Wird geladen…