4-Chlorophenol → HCID 9817423, compound

HRID 1290819Notes

Reaction equation

HRID 1290819 reaction equation
Br[C:2]([C:5]1[N:10]2[N:11]=[CH:12][N:13]=[C:9]2[N:8]=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>C(CC(=O)C)(=O)C.[Ni].C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]([C:5]2[N:10]3[N:11]=[CH:12][N:13]=[C:9]3[N:8]=[CH:7][CH:6]=2)([CH3:4])[CH3:3])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 516892Sodium BicarbonateHCID 18919352HCID 18919352, compound

Product 1

HCID 9817423HCID 9817423, compound

Reagents, catalysts & solvents 2

HCID 54605146HCID 54605146, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 7-(1-bromo-1-methylethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.95 g, prepared in a similar manner to that described above), 4-chlorophenol (1.56 g), sodium bicarbonate (1 g), nickel acetyl acetone (5 mg) and dry toluene (80 ml) was stirred and heated under reflux for 7 days. The solvent was evaporated and the crude product was purified by flash chromatography using as eluent a mixture of toluene and ethylacetate (in the ratio 5:1 respectively), followed by recrystallisation from n-hexane, to give 7-[1-(4-chlorophenoxy)-1-methylethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 0.67 g, (mp 132°-135° C.).

Workup

  1. customprepared in a similar manner to that
  2. temperatureheated
  3. temperatureunder reflux for 7 days
  4. customThe solvent was evaporated
  5. customthe crude product was purified by flash chromatography
  6. additiona mixture of toluene and ethylacetate (in the ratio 5:1 respectively),
  7. customfollowed by recrystallisation from n-hexane

Sources & evidence

ORD record
ord-bfe610c3f7d84b66a288a6a9ecaba643
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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