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

HRID 553254노트

반응식

HRID 553254 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-967dfeee50d744a58cc4b9e2a711ccb5
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951956B2

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