P-Toluenesulfonylhydrazide → HCID 22414560, compound

HRID 1721316Notes

Reaction equation

HRID 1721316 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][C:3]=1[CH3:11].CC1C=CC([S:19]([NH:22][NH2:23])(=O)=O)=CC=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:23]=[N:22][S:19][CH:9]=2)=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 3471241-(4-Bromo-3-methylphenyl)ethanone

Product 1

HCID 22414560HCID 22414560, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-bromo-3-methylphenyl)ethanone (500 mg) and 4-methylbenzenesulphonic acid hydrazide (437 mg) was heated to reflux in ethanol (15 ml) containing a few 4A molecular sieves for 5 h. On cooling, colourless needles were formed, which were collected by filtration (577 mg). 300 mg of this intermediate hydrazone were dissolved in thionyl chloride (2 ml) and was stirred at 20° for 5 h. The mixture was neutralised with 2N sodium carbonate (40 ml) and extracted with ethyl acetate (2×30 ml). The dried extracts were then evaporated to give a yellow solid. This material was chromatographed on silica eluting with dichloromethane;hexane (1:1) to give the title compound as pale yellow solid (167 mg). T.l.c. ethyl acetate:hexane (1:4) Rf 0.52.

Workup

  1. temperaturewas heated
  2. temperatureOn cooling
  3. customcolourless needles were formed
  4. filtrationwhich were collected by filtration (577 mg)
  5. dissolution300 mg of this intermediate hydrazone were dissolved in thionyl chloride (2 ml)
  6. extractionextracted with ethyl acetate (2×30 ml)
  7. customThe dried extracts were then evaporated
  8. customto give a yellow solid
  9. customThis material was chromatographed on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-68b81201ce794faf85e92768f6baef93
Source dataset
uspto-grants-1996_04
Patent number
US05510350

Reaction notes

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