Water → HCID 53801683, compound

HRID 225006Notes

Reaction equation

HRID 225006 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[C:8]([CH:16](Br)[CH:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CN(C)C=O.CCCCCC>[C:8]([CH:16]=[C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 569869312,3-Dibromo-3-(2-chlorophenyl)-1-phenylpropan-1-one

Product 1

HCID 53801683HCID 53801683, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

This Example illustrates the preparation of compound no. 3 of Table I. 1,2,4-Triazole (4.64 g) in dry dimethylformamide (10 ml) was added slowly to a suspension of sodium hydride (2.88 g of 50% dispersion in mineral oil, washed free of oil with dry petrol) in dry dimethylformamide (10 ml) with cooling and stirring. A solution of 1-benzoyl-1,2-dibromo-2-(o-chlorophenyl) ethane (8.45 g) in dry dimethylformamide (10 ml) was then added and the mixture heated at 100° C. for 1 hour. The mixture was poured into cold water (1 liter) and extracted with ether. The ether extracts were dried and evaporated to give a yellow oil. This was dissolved in hexane and the solution cooled to -15° C. The light yellow fibrous crystals were filtered off to give 1-benzoyl-2-o-chlorophenyl-2-(1,2,4-triazol-1-yl)-ethylene (compound no. 3 of Table I) having a melting point of 79°-81° C.

Workup

  1. customthe preparation of compound no
  2. temperaturewith cooling
  3. extractionextracted with ether
  4. dry with materialThe ether extracts were dried
  5. customevaporated
  6. customto give a yellow oil
  7. temperaturethe solution cooled to -15° C
  8. filtrationThe light yellow fibrous crystals were filtered off

Sources & evidence

ORD record
ord-7facab5741704721b7ae08b01f15035e
Source dataset
uspto-grants-1980_11
Patent number
US04235620

Reaction notes

Loading…