1,2-Dibromoethane → HCID 14125894, compound

HRID 1761891Notes

Reaction equation

HRID 1761891 reaction equation
[C:1]1([C:11]([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Br[CH2:22][CH2:23]Br>ClC(Cl)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[N:14]1([C:13]2([C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[O:12])[CH2:23][CH2:22]2)[CH:18]=[N:17][CH:16]=[N:15]1

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 10705024HCID 10705024, compound

Product 1

HCID 14125894HCID 14125894, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

20.7 g (0.1 mol) of (1, 2, 4-triazol-1-yl)-methyl 1-naphthyl ketone in 100 ml of dichloroethane, 0.3 g of benzyltriethyl-ammonium chloride and 27 ml of 50% strength sodium hydroxide solution were placed in a reaction flask, and, under reflux, 20.7 g (0.11 mol) of 1, 2-dibromoethane were added dropwise over 15 minutes. The mixture was refluxed for a further 5 hours, cooled, diluted with water and extracted with di-chloroethane. After drying and removing the solvent, 10.6 g (45% of theory) of the title compound were obtained as an oil.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was refluxed for a further 5 hours
  3. temperaturecooled
  4. extractionextracted with di-chloroethane
  5. customAfter drying
  6. customremoving the solvent, 10.6 g (45% of theory) of the title compound
  7. customwere obtained as an oil

Sources & evidence

ORD record
ord-49d8985747004cb69d6b697de181f8e9
Source dataset
uspto-grants-1989_05
Patent number
US04829075

Reaction notes

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