Dimethylformamide → 2-(2-Formyl-3,5-dimethyl-pyrrol-4-yl)-5-benzoylbenzimidazole

HRID 553237Notes

Reaction equation

HRID 553237 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[NH:13][CH:14]=[C:15]([CH3:34])[C:16]=1[C:17]1[NH:18][C:19]2[CH:25]=[C:24]([C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:23]=[CH:22][C:20]=2[N:21]=1.[OH-].[Na+]>O>[CH:8]([C:14]1[NH:13][C:12]([CH3:11])=[C:16]([C:17]2[NH:18][C:19]3[CH:25]=[C:24]([C:26](=[O:33])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:23]=[CH:22][C:20]=3[N:21]=2)[C:15]=1[CH3:34])=[O:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 579558272-(2,4-Dimethyl-pyrrol-3-yl)-5-benzoylbenzimidazole

Product 1

HCID 579557912-(2-Formyl-3,5-dimethyl-pyrrol-4-yl)-5-benzoylbenzimidazoleYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphoryl chloride (2.43 g) was slowly added dropwise to N,N-dimethylformamide (15.9 g) at room temperature, and stirred at room temperature for 30 minutes. To this mixture, an N,N-dimethylformamide solution of the 2-(2,4-dimethyl-pyrrol-3-yl)-5-benzoylbenzimidazole (2.5 g) obtained in Example 7 was slowly added dropwise. After stirring for 2 hours, 50 ml of a 1 N sodium hydroxide aqueous solution was added, heated to 80° C., and stirred for 2 hours. After the starting material was disappeared, reaction mixture was slowly added to water, and precipitate was collected by filtration. The solid was dried in vacuo to afford 2-(2-formyl-3,5-dimethyl-pyrrol-4-yl)-5-benzoylbenzimidazole (1.63 g, 60%) as a brown solid.

Workup

  1. stirringAfter stirring for 2 hours
  2. temperatureheated to 80° C.
  3. stirringstirred for 2 hours
  4. customreaction mixture
  5. filtrationwas collected by filtration
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-aa4e5ede245340ddb35797041487b7de
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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