Trityl chloride → methyl 1-trityl-1H-1,2,4-triazole-3-carboxylate

HRID 720610Notes

Reaction equation

HRID 720610 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]=[CH:8][NH:7][N:6]=1)=[O:4].[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178499122HCID 178499122, compound

Product 1

HCID 58739241methyl 1-trityl-1H-1,2,4-triazole-3-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1H-[1,2,4]triazole-3-carboxylic acid methyl ester (3.0 g, 0.23 mol) in N,N-dimethylformamide (76 mL) at 25° C. was treated with triphenylmethylchloride (7.2 g, 0.23 mol) and triethylamine (6.41 mL, 0.23 mol). The reaction mixture was stirred at 25° C. for 4 days and then diluted with ethyl acetate. The mixture was then washed with a dilute aqueous hydrochloric acid solution. At this time, methanol was added to the organic layer. A precipitate formed and was removed by filtration. The organics were further washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was triturated with diethyl ether. The solid was collected by filtration and washed again with diethyl ether to afford 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester as a white solid (2.45 g, 84%) which was used without further purification: LR-FAB for C23H19N3O2 (M+) at m/z=369.

Workup

  1. washThe mixture was then washed with a dilute aqueous hydrochloric acid solution
  2. additionAt this time, methanol was added to the organic layer
  3. customA precipitate formed
  4. customwas removed by filtration
  5. washThe organics were further washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting solid was triturated with diethyl ether
  10. filtrationThe solid was collected by filtration
  11. washwashed again with diethyl ether

Sources & evidence

ORD record
ord-09af1ed76ff54fad80c7fec1b9278d58
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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