Trityl chloride → HCID 13471706, compound

HRID 746320Notes

Reaction equation

HRID 746320 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[N:2]1.[C:11](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([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(N(CC)CC)C>C(Cl)(Cl)Cl>[C:11]([N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[N:2]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178469944HCID 178469944, compound

Product 1

HCID 13471706HCID 13471706, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.47 g of ethyl 1,2,3-triazole-4-carboxylate and 7.55 g of trityl chloride were dissolved in 100 ml of chloroform and 3.77 ml of triethylamine was added dropwise thereto under stirring and cooling in an ice-bath. The resulting mixture was stirred for 30 minutes at room temperature. Chloroform was distilled off and the residue was dissolved in ethyl acetate and the mixture was washed with an aqueous solution of sodium chloride and then dried with sodium sulfate. Ethyl acetate was distilled off and the residue was purified by silica gel column chromatography with benzene and chloroform eluent to give 8.37 g of ethyl N-trityl-1,2,3-triazole-4-carboxylate with mp 201°-203° C.

Workup

  1. temperaturecooling in an ice-bath
  2. stirringThe resulting mixture was stirred for 30 minutes at room temperature
  3. distillationChloroform was distilled off
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washthe mixture was washed with an aqueous solution of sodium chloride
  6. dry with materialdried with sodium sulfate
  7. distillationEthyl acetate was distilled off
  8. customthe residue was purified by silica gel column chromatography with benzene and chloroform eluent

Sources & evidence

ORD record
ord-456bae0a376f4d71879ee8edffd5eedb
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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