5,6-Dimethylbenzimidazole → 1H-Furo[3,4-f]benzimidazole-5,7-dione

Reaction equation

[N:1]1[C:5]2[CH:6]=[C:7]([C:13]([OH:15])=[O:14])[C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.CC1C(C)=CC2N=CNC=2C=1>>[N:3]1[C:4]2[CH:9]=[C:8]3[C:10](=[O:12])[O:15][C:13](=[O:14])[C:7]3=[CH:6][C:5]=2[NH:1][CH:2]=1

Participants

Reactant 2

HCID 6755,6-Dimethylbenzimidazole

HCID 7023591Benzimidazole-5,6-dicarboxylic acid

Product 1

HCID 108452781H-Furo[3,4-f]benzimidazole-5,7-dioneYield 81.5%

Conditions

Temperature: 250 °C

Procedure

Benzimidazole-5,6-dicarboxylic acid (8.2 g), prepared from 5,6-dimethylbenzimidazole as described in J.Org.Chem. 1987, 52, 2934., was heated at 250° C. under vacuum (0.01 mm Hg) for 1 h. The solid was extracted with hot acetone and the acetone extracts were evaporated to give the title compound (6.1 g).

Workup

extractionThe solid was extracted with hot acetone
customthe acetone extracts were evaporated

Sources & evidence

ORD record: ord-8d039b3793844ab9a102886c2463afb6
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912260

Reaction notes

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