2-Bromoethyl ethyl ether → HCID 178468143, compound

HRID 1606089Notes

Reaction equation

HRID 1606089 reaction equation
N1C=CN=N1.[Na].[NH:7]1[CH:11]=[N:10][C:9]([SH:12])=[N:8]1.Br[CH2:14][CH2:15][O:16][CH2:17][CH3:18]>C(O)C>[CH2:15]([O:16][CH2:17][CH2:18][S:12][C:9]1[N:10]=[CH:11][NH:7][N:8]=1)[CH3:14]

Participants

6

Reactant 4

HCID 611412-Bromoethyl ethyl etherHCID 5360545SodiumHCID 178418936HCID 178418936, compoundHCID 178527894HCID 178527894, compound

Product 1

HCID 178468143HCID 178468143, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The novel intermediate triazole compounds used in the above preparation were prepared as follows. To a solution of 11.8 g. sodium in 350 ml. absolute ethanol was added 52.5 g. 1,2,4-triazole-3-thiol. To the resulting solution was added 84 g. 1-bromo-2-ethoxyethane and the resulting solution refluxed for 3 hours. The cooled reaction mixture was filtered, the filtrate was evaporated under reduced pressure to remove solvent, and the residue was dissolved in ether. The resulting solution was filtered, the filtrate was evaporated to remove solvent and the residue distilled under reduced pressure to give 3-(2-ethoxyethylthio)-1,2,4-triazole, b.p. 137°-145°C./0.3-0.5 mm. Elemental analysis satisfactory.

Workup

  1. customwere prepared
  2. additionTo the resulting solution was added 84 g
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customto remove solvent
  7. dissolutionthe residue was dissolved in ether
  8. filtrationThe resulting solution was filtered
  9. customthe filtrate was evaporated
  10. customto remove solvent
  11. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-0be057564ee0482f97872a7199e211c4
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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