3-Amino-5-methyl-4H-1,2,4-triazole → 7-[1-(4-Chlorophenoxy)ethyl]-2-methyl-1,2,4-triazolo [1,5-a]pyrimidine

HRID 1290814Notes

Reaction equation

HRID 1290814 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]([CH3:13])C)=[CH:4][CH:3]=1.NC1[N:23]=[C:22]([CH3:24])[NH:21][N:20]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:8]2[N:20]3[N:21]=[C:22]([CH3:24])[N:23]=[C:13]3[N:11]=[CH:10][CH:9]=2)[CH3:15])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 2346103-Amino-5-methyl-4H-1,2,4-triazoleHCID 37226344-(4-Chlorophenoxy)-1-(dimethylamino)pent-1-en-3-one

Product 1

HCID 99040527-[1-(4-Chlorophenoxy)ethyl]-2-methyl-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 (1.58 g, prepared in a similar manner to that described in Example 2 above) in glacial acetic acid (5 ml) was added to a stirred solution of 3-amino-5-methyl-1,2,4-triazole (0.62 g) in glacial acetic acid (10 ml). The mixture was heated under reflux for 2 hours and 30 minutes and then cooled to room temperature. The mixture was then poured into ice-water (50 ml) 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, followed by recrystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 40°-60° C.), to give 7-[1-(4-chlorophenoxy)ethyl]-2-methyl-1,2,4-triazolo [1,5-a]pyrimidine. Yield 1.13 g, (mp 138° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours and 30 minutes
  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. customfollowed by recrystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-6c7bce34c84c4f3da39c9845c10c7419
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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