1H-1,2,4-Triazole → HCID 19811645, compound

HRID 2073381Notes

Reaction equation

HRID 2073381 reaction equation
Br[CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]=[CH:8][C:9]3[O:10][C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[C:13]=32)=[CH:5][CH:4]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>C(#N)C>[CH3:16][C:12]1([CH3:17])[C:11](=[O:18])[O:10][C:9]2[CH:8]=[CH:7][C:6]3[C:14]([C:13]1=2)=[CH:15][C:3]([CH2:2][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)=[CH:4][CH:5]=3

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 19858042HCID 19858042, compound

Product 1

HCID 19811645HCID 19811645, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 8-bromomethyl-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone in acetonitrile (5 ml), was treated with 1,2,4-triazole (1.4 g) and the mixture was heated under reflux for 18 h. The solution was evaporated to dryness under reduced pressure and the residue was partitioned between 1N aqueous sodium hydrogen carbonate and ethyl acetate. The ethyl acetate extract was separated, dried and evaporated to dryness, and the residue was purified by flash chromatography. Elution with methanol:chloroform, 1:49 v/v, gave 1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2-(1H)-naphtho[2,1-b]furanone, m.p. 136°-137° after recrystallisation from a mixture of ethyl acetate and cyclohexane.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. customThe solution was evaporated to dryness under reduced pressure
  4. customthe residue was partitioned between 1N aqueous sodium hydrogen carbonate and ethyl acetate
  5. extractionThe ethyl acetate extract
  6. customwas separated
  7. customdried
  8. customevaporated to dryness
  9. customthe residue was purified by flash chromatography
  10. washElution with methanol

Sources & evidence

ORD record
ord-816674251361436b9d3d5eee15484346
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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