4'-Hydroxyacetophenone → HCID 9817222, compound

HRID 1290805Notes

Reaction equation

HRID 1290805 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[H-].[Na+].Br[CH:14]([C:16]1[N:21]2[N:22]=[CH:23][N:24]=[C:20]2[N:19]=[CH:18][CH:17]=1)[CH3:15]>COCCOC>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:14]([C:16]2[N:21]3[N:22]=[CH:23][N:24]=[C:20]3[N:19]=[CH:18][CH:17]=2)[CH3:15])=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 24758Sodium hydrideHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Product 1

HCID 9817222HCID 9817222, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 4-hydroxyacetophenone (1.36 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 above) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The reaction mixture was stirred at room temperature for 24 hours. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the mixture and the residue was dissolved in dichloromethane and washed with 200 ml of a 5% aqueous solution of sodium hydroxide followed by water. Evaporation of the solvent afforded a crude product which was recrystallised from ethyl acetate, to give 7-[1-(4-acetylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 0.87 g, (m.p. 136°-138° C.).

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at room temperature for 24 hours
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the mixture
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with 200 ml of a 5% aqueous solution of sodium hydroxide
  7. customEvaporation of the solvent
  8. customafforded a crude product which
  9. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-79f629325ce14a40a662cdbf6f790f62
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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