Toluene → 3-Cyclohexylpropyl 3-(1H-imidazol-4-yl)propyl ether

HRID 744035

반응식

HRID 744035 반응식
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O-:16])[N:10]=[CH:9]2)C=CC=CC=1.[Na+].C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOC1.Cl[CH2:53][CH2:54][CH2:55][CH:56]1[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>C(OCC)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:16][CH2:53][CH2:54][CH2:55][CH:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)[N:10]=[CH:9]1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 3633615-Crown-5HCID 70762(3-Chloropropyl)cyclohexaneHCID 23682245sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate

생성물 1

HCID 1784208943-Cyclohexylpropyl 3-(1H-imidazol-4-yl)propyl ether

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
75 °C

실험 절차

5 mmol of sodium 3-[1-(triphenylmethyl)imidazol-4-yl]propoxide in 10 ml of toluene containing 0.5 mmol of 15-Crown-5 and 5 mmol of (3-chloropropyl)cyclohexane are mixed and the mixture is stirred for 24 h at 75° C. The suspension is concentrated under vacuum, the product obtained is dissolved in diethyl ether, the solution is filtered and the residue washed with petroleum ether (40°-60° C.). The filtrate obtained is concentrated and maintained for 1 h at the boiling point in a 2N aqueous/alcohol (ethanol/water) hydrochloric acid solution. The ethanol is removed under a low vacuum and the precipitate is filtered under vacuum. The solution is basified, extracted with dichloromethane and the organic phase is concentrated. The title compound obtained is recrystallized in the hydrogenmaleate form from ethanol/diethyl ether.

후처리

  1. concentrationThe suspension is concentrated under vacuum
  2. customthe product obtained
  3. filtrationthe solution is filtered
  4. washthe residue washed with petroleum ether (40°-60° C.)
  5. customThe filtrate obtained
  6. concentrationis concentrated
  7. temperaturemaintained for 1 h at the boiling point in a 2N aqueous/alcohol (ethanol/water) hydrochloric acid solution
  8. customThe ethanol is removed under a low vacuum
  9. filtrationthe precipitate is filtered under vacuum
  10. extractionextracted with dichloromethane
  11. concentrationthe organic phase is concentrated

출처 및 근거

ORD 기록
ord-00b6922018944aca9cf64b1932ec59e1
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559113

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