4-(4-Chlorophenoxy)-1-(dimethylamino)pent-1-en-3-one → 7-[1-(4-Chlorophenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1290797Notes

Reaction equation

HRID 1290797 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]([CH3:15])[C:8](=O)[CH:9]=[CH:10][N:11](C)[CH3:12])=[CH:4][CH:3]=1.[NH2:18][C:19]1N=C[NH:21][N:20]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]([C:8]2[N:21]3[N:20]=[CH:19][N:18]=[C:12]3[N:11]=[CH:10][CH:9]=2)[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 37226344-(4-Chlorophenoxy)-1-(dimethylamino)pent-1-en-3-oneHCID 178418311HCID 178418311, compound

Product 1

HCID 38017397-[1-(4-Chlorophenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 4-(4-chlorophenoxy)-1-(dimethylamino)-1-penten-3-one (9.80 g) in glacial acetic acid (50 ml) was added to a stirred solution of 3-amino-1,2,4-triazole (3.25 g) in glacial acetic acid (50 ml). The mixture was heated under reflux for 5 hours and then cooled to room temperature. The mixture was then poured into 300 ml of ice-water and extracted with toluene. The toluene extracts were washed with a 10% aqueous solution of sodium hydrogen carbonate, followed by water, then dried over anhydrous magnesium sulphate and the solvent was evaporated under reduced pressure. The residue was triturated with cold diethyl ether and the solid was collected by filtration and recrystallised from a mixture of ethyl acetate and petroleum ether (b.p. 40°-60° C.), to give 7-[1-(4-chlorophenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 6.91 g, (mp 111°-112° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted with toluene
  4. washThe toluene extracts were washed with a 10% aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was triturated with cold diethyl ether
  8. filtrationthe solid was collected by filtration
  9. customrecrystallised from a mixture of ethyl acetate and petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-04053744f792402780950a6cabc500b6
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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