Carbon Dioxide → 1-Benzylbenzimidazole-2-carboxylic acid

HRID 982026

Reaktionsgleichung

[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22](=[O:24])=[O:23].O>O1CCCC1>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:22]([OH:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 2.08 g (10 mmol) of 1-benzylbenzimidazole in 200 ml of dry tetrahydrofuran was cooled under N2 atmosphere to -78° C. and treated with 8.0 ml (20 mmol) of n-butyllithium. The resulting solution was warmed to 0° C. for 0.5 h, recooled to -78° C., and poured into a mixture of excess dry ice in 200 ml of tetrahydrofuran. After being allowed to warm, the solution was treated with 200 ml of water, washed with ether, neutralized, and washed with ether. The aqueous layer was concentrated in vacuo, after which the residue was triturated with 2% methanol in chloroform and filtered. The filtrate was dried over MgSO4 and concentrated to give 2.01 g (80%) of the desired compound as a white powder. Mass spectrum: (M-OH)+ =235.

Aufarbeitung

customrecooled to -78° C.
temperatureto warm
washwashed with ether
washneutralized, and washed with ether
concentrationThe aqueous layer was concentrated in vacuo
customafter which the residue was triturated with 2% methanol in chloroform
filtrationfiltered
dry with materialThe filtrate was dried over MgSO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-750c5365c4094d608c2b9ce6794daa31
Quelldatensatz: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04994477

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