Water → 1-Trityl-1,2,4-triazole-3-carboxylic acid ethyl ester

HRID 2307538Notes

Reaction equation

HRID 2307538 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2].C(N(CC)C(C)C)(C)C.[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.O>CN(C=O)C.C(OC(=O)C)C>[CH2:1]([O:3][C:4]([C:6]1[N:10]=[CH:9][N:8]([C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 178418794HCID 178418794, compound

Product 1

HCID 574241681-Trityl-1,2,4-triazole-3-carboxylic acid ethyl esterYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 60 ml of DMF was dissolved 7.62 g (54 mmol) of 1H-1,2,4-triazole-3-carboxylic acid ethyl ester. To the solution were added at room temperature 14 g (108 mmol) of N,N-diisopropylethylamine and 15.8 g (56.7 mmol) of tritylchloride. The mixture was stirred for 2 hours. 300 ml of water and 300 ml of ethylacetate were added thereto. The crystal was filtered, dissolved in 150 ml of chloroform, washed with water and dried. The solvent was removed. The residue was crystallized from ether to give 8.91 g of the titled compound. The ethylacetate layer was washed with water, dried and evaporated. The residue was crystallized from ether to give 4.73 g of the titled compound. 13.64 g of 1-trityl-1,2,4-triazole-3-carboxylic acid ethyl ester was totally obtained. Yield: 66%.

Workup

  1. filtrationThe crystal was filtered
  2. dissolutiondissolved in 150 ml of chloroform
  3. washwashed with water
  4. customdried
  5. customThe solvent was removed
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-f1877809efc24161ad45332422070b69
Source dataset
uspto-grants-2004_12
Patent number
US06831177B1

Reaction notes

Loading…