p-Toluenesulfonic acid → HCID 85772042, compound

HRID 436356Notes

Reaction equation

HRID 436356 reaction equation
[CH3:1][C:2](=O)[C:3]([CH3:6])([CH3:5])[CH3:4].[C:8]([NH:12][NH2:13])([CH3:11])([CH3:10])[CH3:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:8]([NH:12][N:13]=[C:2]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH3:1])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6416PinacoloneHCID 81890tert-Butylhydrazine

Product 1

HCID 85772042HCID 85772042, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5 g. (.05 m.) pinacolone in 50 ml. benzene was added 5 g. (.057 m.) tert.-butylhydrazine and a spatula tip of para-toluenesulfonic acid. The flask was fitted with a Dean Stark trap and the reaction refluxed until 0.9 ml. (.05 m.) of water was azeotroped off. The solution was cooled down and the benzene stripped off leaving 8.5 g. (100%) of a white fluffy solid. The infra-red spectrum of the solid was consistent with the structure of the proposed compound.

Workup

  1. customThe flask was fitted with a Dean Stark trap
  2. temperaturethe reaction refluxed until 0.9 ml
  3. custom(.05 m.) of water was azeotroped off
  4. temperatureThe solution was cooled down
  5. customleaving 8.5 g

Sources & evidence

ORD record
ord-c576528cc5e044189af15ca213a886f9
Source dataset
uspto-grants-1977_02
Patent number
US04008273

Reaction notes

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