Sodium Carbonate → 4-(5-Phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid ethyl ester

HRID 553254Notes

Reaction equation

HRID 553254 reaction equation
S([O-])(O)=O.[Na+].[CH2:6]([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])[CH3:7].[O:20]([C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[C:29]([NH2:34])[CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[CH2:6]([O:8][C:9]([C:11]1[NH:12][C:13]([CH3:19])=[C:14]([C:17]2[NH:34][C:29]3[CH:28]=[C:27]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:32]=[CH:31][C:30]=3[N:33]=2)[C:15]=1[CH3:16])=[O:10])[CH3:7]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 1374862199-64-6HCID 106556434-Phenoxybenzene-1,2-diamineHCID 23665763Sodium Bisulfite

Product 1

HCID 579558234-(5-Phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid ethyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

Sodium hydrogensulfite (0.87 g, 8.4 mmol) and 3,5-dimethyl-4-formylpyrrole-2-carboxylic acid ethyl ester (1.64 g, 8.4 mmol) were added to an N,N-dimethyl acetamide (25 ml) solution of 4-phenoxy-1,2-phenylenediamine (1.60 g, 8.0 mmol) reported in the references, and the reaction mixture was heated to 110° C. and stirred for 18 hours. The reaction mixture was allowed to cool to room temperature, and a 5% sodium carbonate was added. The mixture was extracted with ethyl acetate, and the extract was washed with water and a saturated sodium chloride, and then dried with anhydrous sodium sulfate. The desiccant was filtered off, and then the residue obtained by evaporation at reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:100 to 1:30) to afford 4-(5-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid ethyl ester (2.27 g, 76%) as a light yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materiala saturated sodium chloride, and then dried with anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. customthe residue obtained by evaporation at reduced pressure
  7. customwas purified

Sources & evidence

ORD record
ord-967dfeee50d744a58cc4b9e2a711ccb5
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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