Thionyl Chloride → 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole

HRID 349927ノート

反応式

HRID 349927 の反応式
S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([CH2:23]O)[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([CH2:23][Cl:3])[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 23025093(1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol

生成物 1

HCID 230250441-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole収率 96.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Thionyl chloride (4.35 g) was added to a solution of (1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol (8.06 g) in toluene (100 ml) dropwise at 0° C., and the mixture was stirred at room temperature for one hour and then refluxed for ten minutes. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole (8.31 g, yield: 96%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

後処理

  1. temperaturerefluxed for ten minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5da7c8d0132c42a28530ec8bb0aaa86b
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

読み込み中…