Acetic Acid → (5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol

HRID 1857691

반응식

HRID 1857691 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH:16]=[O:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[BH4-].[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.CCCCCC>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:3]=[C:2]([Cl:1])[CH:7]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 4739155-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

생성물 1

HCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol수율 79%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8058Hexane용매

실험 절차

In 4 ml of ethanol was dissolved 440 mg (1.3 mmol) of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound I-6), followed by addition of 51 mg (1.3 mmol) of sodium borohydride at room temperature. After 10 minutes, the mixture was neutrized by acetic acid and sodium bicarbonate, and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was then concentrated under reduced pressure and the residue was recrystallized by isopropyl ether:n-hexane to provide 340 mg (yield 77%) of Compound I-8. mp 157 to 158° C.

후처리

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was then concentrated under reduced pressure
  5. customthe residue was recrystallized by isopropyl ether

출처 및 근거

ORD 기록
ord-b473258185a94bd080166a739be37259
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147097

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