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

HRID 249589Notes

Reaction equation

HRID 249589 reaction equation
[Na].[NH:2]1[CH:6]=[C:5]([SH:7])[N:4]=[N:3]1.[S:8]1[CH:12]=C[CH:10]=[C:9]1CC(OCCl)=O.[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1.CN(C)C=[O:48]>ClCCl>[C:9]([S:8][CH2:12][S:7][C:5]1[N:4]=[N:3][N:2]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=1)(=[O:48])[CH3:10]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 57186933Chloromethyl thiolacetateHCID 178527739HCID 178527739, compound

Product 1

HCID 103734144-Acetylthiomethylthio-1-trityl-1,2,3-triazoleYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,2,3-triazol-4-thiol sodium salt (109 g : 870 mMol.) in dimethylformamide (300 ml) is added dropwise at -20° to -30° C. chloromethyl thiolacetate (109 g : 870 mMol.), and the mixture is stirred at room temperature for 2 hours. To the reaction mixture are added under ice cooling trityl chloride (292 g; 1.05 Mol.) and pyridine (84.6 ml : 1.05 Mol.), and the mixture is stirred at room temperature for 18 hours, diluted with dichloromethane, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is crystallized from ether to give 4-acetylthiomethylthio-1-trityl-1,2,3-triazole (183 g). Yield: 49%. mp. 115° to 116° C. Colorless crystals.

Workup

  1. additionTo the reaction mixture are added under ice
  2. stirringthe mixture is stirred at room temperature for 18 hours
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-c23f05ae3e7145998227b2133ecc1d47
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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