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

HRID 1416305Notes

Reaction equation

HRID 1416305 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

3

Reactant 2

HCID 6755,6-DimethylbenzimidazoleHCID 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

  1. extractionThe solid was extracted with hot acetone
  2. customthe acetone extracts were evaporated

Sources & evidence

ORD record
ord-8d039b3793844ab9a102886c2463afb6
Source dataset
uspto-grants-1999_06
Patent number
US05912260

Reaction notes

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