3-Chlorophenol → 7-[1-(3-Chlorophenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1290809Notes

Reaction equation

HRID 1290809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH:12]([C:14]1[N:19]2[N:20]=[CH:21][N:22]=[C:18]2[N:17]=[CH:16][CH:15]=1)[CH3:13]>COCCOC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:12]([C:14]1[N:19]2[N:20]=[CH:21][N:22]=[C:18]2[N:17]=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Product 1

HCID 33262607-[1-(3-Chlorophenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 3-chlorophenol (1.28 g) in dry 1,2-dimethoxyethane was added slowly to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g, prepared in a similar manner to that described in Example 6) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The reaction mixture was stirred overnight at room temperature, filtered and the solvent was evaporated from the filtrate under reduced pressure. The residue was purified by flash chromatography using as eluent a mixture of ethyl acetate and petroleum ether to give 7-[1-(3-chlorophenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 2.11 g, (mp 124°-126° C.).

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. filtrationfiltered
  4. customthe solvent was evaporated from the filtrate under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. additiona mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-4a07c71cfc3c4cd998eaedaa1828ac10
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

Loading…