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Pyridine → 3-Acetylthiomethylthio-1-trityl-1,2,4-triazole

HRID 249577
ノート
印刷プレビュー

反応式

HRID 249577 の反応式
[NH:1]1[CH:5]=[N:4][C:3]([SH:6])=[N:2]1.[H-].[Na+].[S:9]1[CH:13]=C[CH:11]=[C:10]1CC(OCCl)=O.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1.CN(C)C=[O:49]>O>[C:10]([S:9][CH2:13][S:6][C:3]1[N:4]=[CH:5][N:1]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:2]=1)(=[O:49])[CH3:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 1049PyridineHCID 6228Dimethylformamide2 回HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 57186933Chloromethyl thiolacetateHCID 178527894HCID 178527894、化合物

生成物 1

HCID 10094304
3-Acetylthiomethylthio-1-trityl-1,2,4-triazole
収率 39%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 1,2,4-triazole-3-thiol (2.23 g : 22.1 mMol.) in dimethylformamide (30 ml) is added sodium hydride (60% in oil : 840 mg : 21 mMol.), and the mixture is stirred at room temperature for 10 minutes. To this solution at -50° to -60° C. is added a solution of chloromethyl thiolacetate (2.50 g : 20.1 mMol.) in dimethylformamide (5 ml), and the mixture is stirred at the same temperature for 20 minutes, mixed with another trityl chloride (6.70 g : 24 mMol.) and pyridine (1.94 ml : 24.0 mMol.), stirred under ice cooling for 28 hours, diluted with water, and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1) and crystallized from ether to give 3- acetylthiomethylthio-1-trityl-1,2,4-triazole (3.37 g). Yield: 39%. Colorless crystals, mp. 124° to 125° C.

後処理

  1. stirringthe mixture is stirred at the same temperature for 20 minutes
  2. stirringstirred under ice cooling for 28 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1)
  8. customcrystallized from ether

出典と根拠

ORDレコード
ord-67ed221eae5f46d6be57cfb93f394733
出典データセット
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05214037

反応ノート

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