Sodium Bicarbonate → (1-(2-Hydroxypropyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)methanol

HRID 1857784노트

반응식

HRID 1857784 반응식
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][CH:28]([OH:30])[CH3:29])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>Cl>[Cl:26][C:21]1[CH:20]=[C:19]([S:18][C:12]2[N:11]([CH2:27][CH:28]([OH:30])[CH3:29])[C:10]([CH2:9][OH:8])=[N:14][C:13]=2[CH:15]([CH3:17])[CH3:16])[CH:24]=[C:23]([Cl:25])[CH:22]=1

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 221303532-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole

생성물 1

HCID 473941(1-(2-Hydroxypropyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)methanol수율 84.5%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
110 °C

실험 절차

In 55 ml of concentrated hydrochloric acid was dissolved 13.4 g (28.7 mmol) of the alcohol (140a), and after the mixture was stirred with heating at 110° C. for 2 hours, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture. The mixture was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (methylene chloride-ethyl acetate=9:1), the oil was treated with ether and crystallized to provide 9.1 g (yield 84%) of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole (141a). mp 159-161° C.

후처리

  1. distillationThe mixture was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (methylene chloride-ethyl acetate=9:1)
  7. additionthe oil was treated with ether
  8. customcrystallized

출처 및 근거

ORD 기록
ord-0199b75303d940a79668a41f5ec8f049
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147097

반응 노트

불러오는 중…