Dimethylformamide → HCID 178526912, compound

HRID 1419176Notes

Reaction equation

HRID 1419176 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:20]=[CH:19][C:15]4[NH:16][CH:17]=[N:18][C:14]=4[CH:13]=3)[CH:10]=2)[NH:5][CH:4]=1)=O.C([O-])(=O)C.[NH4+].[N+:26]([CH3:29])([O-:28])=[O:27].CN(C)C=O>CS(C)=O>[N+:26]([CH:29]=[CH:1][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:20]=[CH:19][C:15]4[NH:16][CH:17]=[N:18][C:14]=4[CH:13]=3)[CH:10]=2)[NH:5][CH:4]=1)([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 178519850HCID 178519850, compound

Product 1

HCID 178526912HCID 178526912, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-(3-formylindol-5-yl)-1H-benzimidazole (0.40 g, 1.53 mmol) and ammonium acetate (50 mg) in a solution of nitromethane (10 mL), N,N-dimethylformamide (5 mL), and dimethyl sulfoxide (1 mL) was heated at reflux under nitrogen for 4 hours. The resulting reaction mixture was cooled to room temperature and filtered to afford the title compound (0.40 g, 86%) as a yellow solid: mp >280° C.; 13C NMR (DMSO-d6) δ 146.9, 145.3, 144.3, 137.4, 136.6, 135.5, 134.2, 132.1, 129.8, 127.8, 125.0, 119.9, 118.7, 115.9, 113.4, 108.7. Anal. calcd for C16H11N5O2.0.125 H2O: C, 62.49; H, 3.69; N, 22.77. Found: C, 62.34; H, 3.51; N, 22.45.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 4 hours
  3. customThe resulting reaction mixture
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0c6a26145ff940feac40090901866cdb
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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