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

HRID 1857691ノート

反応式

HRID 1857691 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b473258185a94bd080166a739be37259
出典データセット
uspto-grants-2000_11
特許番号
US06147097

反応ノート

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