Acetic Acid → ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate

HRID 75485노트

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HRID 75485 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:13])[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Br[CH2:20][C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].CC(O)=O>CC(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:20]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:13]=[C:9]2[CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 66144Ethyl bromopyruvate2회HCID 516892Sodium BicarbonateHCID 178449876HCID 178449876, 화합물2회

생성물 1

HCID 54579226ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate수율 25%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
85 °C

실험 절차

To a solution of N-(4-chlorophenyl)butyrimidamide (compound 3, 3.5 g, 17.80 mmol), NaHCO3 (3.14 g, 37.38 mmol) in i-PrOH was added ethyl bromopyruvate (compound 4, 4.7 mL, 37.38 mmol) under N2. The reaction mixture was stirred at 85° C. for 72 hrs, then added AcOH (15 mL). After 4 hrs, the mixture was concentrated under reduced pressure. The residue was diluted with H2O, and extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3 and 1N-HCl solution, then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage Isolera™ FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane) to provide the title compound (1.28 g, 25%) as a brown oil.

후처리

  1. waitAfter 4 hrs
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with H2O
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with saturated NaHCO3 and 1N-HCl solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography (Biotage Isolera™ FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane)

출처 및 근거

ORD 기록
ord-2cd7dc2d80d24989bc3361bc4bc8049d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835436B2

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