p-Toluenesulfonic acid → HCID 178440675, compound

HRID 274871Notes

Reaction equation

HRID 274871 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=O)=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:3][C:1]([C:5]1[CH:6]=[C:7]2[C:8]([N:9]=[C:18]3[C:17](=[C:15]2[OH:14])[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][CH:11]=1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 698614-Tert-ButylanilineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 178440675HCID 178440675, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution prepared from 25.0 g of 4-t-butylaniline-29.0 g of 2-ethoxycarbonylcyclohexanone, 100 ml of benzene and 0.20 g of p-toluenesulfonic acid was refluxed for 6 hours. At the end of this time no more water was collected from the reaction (Dean-Stark trap), so the benzene was evaporated and the residue was dissolved in 80 ml of diphenyl ether. This mixture was refluxed for 1 hour and then allowed to cool to room temperature overnight. The product which had precipitated from this solution was filtered off and washed well with diethyl ether to give 11.52 g of analytically pure product, m.p. 320°-322°.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customAt the end of this time no more water was collected from the reaction (Dean-Stark trap)
  3. customso the benzene was evaporated
  4. dissolutionthe residue was dissolved in 80 ml of diphenyl ether
  5. temperatureThis mixture was refluxed for 1 hour
  6. customThe product which had precipitated from this solution
  7. filtrationwas filtered off
  8. washwashed well with diethyl ether
  9. customto give 11.52 g of analytically pure product, m.p. 320°-322°

Sources & evidence

ORD record
ord-6440c3e25a844058b3ecf91fe59ec6fd
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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