Thionyl Chloride → HCID 54543988, compound
Reaction equation
[N:1]1([CH2:6][C:7]2[CH:18]=[CH:17][C:10]3[NH:11][C:12]([C:14](O)=[O:15])=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O>>[N:1]1([CH2:6][C:7]2[CH:18]=[CH:17][C:10]3[N:11]4[C:14](=[O:15])[C:12]5=[N:11][C:10]6[CH:17]=[CH:18][C:7]([CH2:6][N:1]7[CH:5]=[CH:4][N:3]=[CH:2]7)=[CH:8][C:9]=6[N:13]5[C:14](=[O:15])[C:12]4=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1Participants
Procedure
A mixture of 2.3 parts of 5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole-2-carboxylic acid and 80 parts of thionyl chloride was stirred for 3 hours at reflux temperature. The reaction mixture was evaporated to dry, yielding 4.3 parts of 3,9-bis(1H-imidazol-1-yl-methyl)-6H,13H-pyrazino[1,2-a:4,5-a']bisbenzimidazole6,13-dione which were poured into a solution of 3.8 parts of sodium methoxide in 40 parts of methanol. The whole was stirred for 1 hour at room temperature. The whole was neutralised with 10 parts of acetic acid and concentrated to dry. The concentrate was taken up in a sodium hydrogen carbonate solution 10% and the product was extracted with a mixture of dichloromethane and methanol (90:10 by volume). The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 0.7 parts (26.9%) of methyl 5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole-2-carboxylate; mp. 228° C. (compound 267).
Workup
- temperatureat reflux temperature
- customThe reaction mixture was evaporated
- customto dry
Sources & evidence
- ORD record
- ord-56941ab6996b4d14ba6f8ba836ee528c
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859684
Reaction notes
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