Trityl chloride → Benzene, 1,1',1''-(azidomethylidyne)tris-

HRID 1707463Notes

Reaction equation

HRID 1707463 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O.O>[C:5]([N:1]=[N+:2]=[N-:3])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 33557Sodium Azide

Product 1

HCID 84340Benzene, 1,1',1''-(azidomethylidyne)tris-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium azide (19.0 g: 0.283 Mol.) in dimethyl-formamide (130 ml) is added trityl chloride (76.0 g: 0.273 Mol.), and the mixture is stirred at room temperature for 5 hours. The reaction mixture is diluted with water and extracted with ether. The extract is washed with brine, dried over sodium sulfate, and concentrated to give trityl azide. To a solution of this azide in acetone (300 ml) is added methyl propiolate (24 ml: 0.27 Mol.), and the mixture is heated under reflux for 6 days. The reaction mixture is cooled to the room temperature and diluted with ether. The separating crystals are collected by filtration to give 1-trityl-1,2,3-triazol-4-ylcarboxylic acid methyl ester (62.0 g) as colorless crystals.

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b026849742ad480e9c539efe8623ee8f
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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