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

HRID 249577
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HRID 249577 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 6

HCID 1049PyridineHCID 6228Dimethylformamide2회HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 57186933Chloromethyl thiolacetateHCID 178527894HCID 178527894, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67ed221eae5f46d6be57cfb93f394733
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05214037

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