1,4-Dichlorobutane → 1-(4-chlorobutyl)-2-methyl-1H-benzimidazole

HRID 354929

Reaktionsgleichung

[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[OH-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17]Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[CH3:1]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a stirred mixture of 13.2 parts of 2-methyl-1H-benzimidazole, 3 parts of N,N,N-triethylbenzenemethanaminium chloride and 225 parts of a sodium hydroxide solution 60% are added 25 parts of 1,4-dichlorobutane. The whole is heated to about 100° C. and stirring is continued for one hour at this temperature. The reaction mixture is cooled and poured onto ice-water. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10) as eluent. The pure fractions are collected and eluent is evaporated, yielding 1-(4-chlorobutyl)-2-methyl-1H-benzimidazole as a residue.

Aufarbeitung

temperatureThe reaction mixture is cooled
additionpoured onto ice-water
extractionThe product is extracted with methylbenzene
customThe extract is dried
filtrationfiltered
customevaporated
customThe residue is purified by column-chromatography over silica gel using
additiona mixture of trichloromethane and methanol (90:10) as eluent
customThe pure fractions are collected
customeluent is evaporated

Quellen und Nachweise

ORD-Eintrag: ord-aad1cf0576ab4c43baf7b66515b146ac
Quelldatensatz: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04377578

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