Triethylamine → 2-Isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester

HRID 1910796노트

반응식

HRID 1910796 반응식
Br[CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C.[CH:26]([C:29]1[NH:30][CH:31]=[CH:32][N:33]=1)([CH3:28])[CH3:27]>CN(C=O)C.O>[CH:26]([C:29]1[N:30]([CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=2[CH:15]([CH3:17])[CH3:16])[CH:31]=[CH:32][N:33]=1)([CH3:28])[CH3:27]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 671063212-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester

생성물 1

HCID 671069432-Isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester수율 43.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

2-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester (0.19 g, 0.6 mmol) was dissolved in DMF (5 mL), then triethylamine (0.5 mL, 3.6 mmol) and 2-isopropylimidazole (0.2 g, 1.8 mmol) were added. The mixture was heated at reflux for 15 h then allowed to cool, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (60-120 mesh), eluting with ethyl acetate, to afford 2-isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester (90 mg, 43%) as an oil.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography on silica gel (60-120 mesh)
  9. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-910ae62a44824098a08c9d1881ef5e13
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604029B2

반응 노트

불러오는 중…