Acetaldehyde → Acetaldehyde 1-benzoyl-1-(2-bromophenyl)hydrazone

HRID 1605100

Reaktionsgleichung

Reaktionsgleichung von HRID 1605100
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].[CH:10](=[O:12])[CH3:11].CCO[CH2:16][CH3:17]>>[C:10]([N:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[N:9]=[CH:16][CH3:17])(=[O:12])[C:11]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Komponenten

4

Edukt 3

HCID 177AcetaldehydeHCID 3283Diethyl EtherHCID 85583(2-Bromophenyl)hydrazine

Produkt 1

HCID 68139504Acetaldehyde 1-benzoyl-1-(2-bromophenyl)hydrazone

Versuchsvorschrift

The acetaldehyde 1-benzoyl-1-(2-bromophenyl) hydrazone was prepared as follows: A solution of 11.2 g. of 2-bromophenyl hydrazine in ether was treated with 7 ml. of acetaldehyde and allowed to stand for 1 hour with occasional swirling. The ether solution was washed with water, a small amount of dilute potassium bicarbonate solution, and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was taken up in 25 ml. dry dimethylformamide and the resulting solution was added dropwise, with stirring and water-bath cooling, to a mixture of 1.56 g. of sodium hydride in 25 ml. dry dimethylformamide and stirring was continued for 1 hour. To this solution under nitrogen was added dropwise with stirring a solution of 7 ml. of benzoyl chloride in 10 ml. of dimethylformamide and stirring was continued for 4 hours. The mixture was diluted with ether and treated with water containing sufficient glacial acetic acid to neutralize excess alkali. The ether extract was washed with water, dilute potassium carbonate solution, water, and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give acetaldehyde 1-benzoyl-1-(2-bromophenyl) hydrazone which was used as such in the above reaction.

Aufarbeitung

  1. customThe acetaldehyde 1-benzoyl-1-(2-bromophenyl) hydrazone was prepared
  2. washThe ether solution was washed with water
  3. dry with materiala small amount of dilute potassium bicarbonate solution, and saturated sodium chloride solution, dried over magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. additiondry dimethylformamide and the resulting solution was added dropwise
  6. temperaturewater-bath cooling, to a mixture of 1.56 g
  7. stirringdry dimethylformamide and stirring
  8. waitwas continued for 1 hour
  9. additionTo this solution under nitrogen was added dropwise
  10. stirringwith stirring a solution of 7 ml
  11. stirringof dimethylformamide and stirring
  12. waitwas continued for 4 hours
  13. additionThe mixture was diluted with ether
  14. additiontreated with water containing sufficient glacial acetic acid
  15. extractionThe ether extract
  16. washwas washed with water, dilute potassium carbonate solution, water, and saturated sodium chloride solution
  17. dry with materialdried over magnesium sulfate
  18. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4e937df69944ff283856e057adfe58a
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03948939

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