Sodium Carbonate → 4-(5-Benzoylbenzimidazol-2-yl)-dimethylpyrrole-2-carboxylic acid

HRID 553238Notes

Reaction equation

HRID 553238 reaction equation
S([O-])(O)=O.[Na+].C([O:8][C:9]([C:11]1[NH:12][C:13]([CH3:19])=[C:14]([CH:17]=O)[C:15]=1[CH3:16])=[O:10])C.[NH2:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[NH2:35])[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[C:24]([C:23]1[CH:32]=[CH:33][C:34]2[N:35]=[C:17]([C:14]3[C:15]([CH3:16])=[C:11]([C:9]([OH:8])=[O:10])[NH:12][C:13]=3[CH3:19])[NH:20][C:21]=2[CH:22]=1)(=[O:25])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 1355203,4-DiaminobenzophenoneHCID 1374862199-64-6HCID 23665763Sodium Bisulfite

Product 1

HCID 160408334-(5-Benzoylbenzimidazol-2-yl)-dimethylpyrrole-2-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium hydrogensulfite (1.0 g) and 3,5-dimethyl-4-formylpyrrole-2-carboxylic acid ethyl ester (1.5 g) were added to an N,N-dimethylacetamide (20 ml) solution of 3,4-diaminobenzophenone (1.6 g), and the mixture was heated to 120° C. and stirred for 10 hours. After the mixture was allowed to cool to room temperature, a 5% sodium carbonate (60 g) was added and stirred at room temperature, and the precipitate was collected by filtration and washed with water. The obtained solid was dissolved in ethanol (15 ml) and tetrahydrofuran (15 ml), and a 4 N sodium hydroxide aqueous solution (20 ml) was added and heated under reflux for 12 hours. After the starting material was disappeared, the reaction mixture was allowed to cool to room temperature, and neutralized with a 1 N hydrochloric acid solution. The precipitate was collected by filtration to afford 4-(5-benzoylbenzimidazol-2-yl)-dimethylpyrrole-2-carboxylic acid (2.3 g, 90%) as a light yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. stirringstirred at room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. dissolutionThe obtained solid was dissolved in ethanol (15 ml)
  6. additiontetrahydrofuran (15 ml), and a 4 N sodium hydroxide aqueous solution (20 ml) was added
  7. temperatureheated
  8. temperatureunder reflux for 12 hours
  9. temperatureto cool to room temperature
  10. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9c4ed00d41204e4ba00a11f8ac37f6c9
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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