Imidazole → HCID 12784623, compound

HRID 1649293Notes

Reaction equation

HRID 1649293 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:18][O:17]1.O>CN(C)C=O>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]([OH:17])([CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)[CH2:18][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-

Product 1

HCID 12784623HCID 12784623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Sodium hydride (50% suspension in oil--2.23 g) was suspended in dimethylformamide (30 ml) under an atmosphere of argon, and cooled in a water bath while imidazole (3.2 g) was added in portions. A solution of 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane (6.4 g) in dimethylformamide (30 ml) was added, and the mixture was heated at 80° C. for 2 hours. The mixture was cooled, poured into water (200 ml) and extracted with methylene dichloride. The organic extract was washed with water twice and with brine twice, dried over sodium sulphate and filtered. The solvent was evaporated under reduced pressure, and the residue was chromatographed on a K60 silica column, eluting with 0 to 7% of methanol in methylene dichloride, to give 2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-(1,2,4-triazol-1-yl)-2-propanol, m.p. 169°-170° C.

Workup

  1. additionwas added in portions
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene dichloride
  4. extractionThe organic extract
  5. washwas washed with water twice
  6. dry with materialwith brine twice, dried over sodium sulphate
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was chromatographed on a K60 silica column
  10. washeluting with 0 to 7% of methanol in methylene dichloride

Sources & evidence

ORD record
ord-f274c7e076774889b7f93b60f65770de
Source dataset
uspto-grants-1983_11
Patent number
US04416682

Reaction notes

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