Water → HCID 178442815, compound

HRID 274867Notes

Reaction equation

HRID 274867 reaction equation
[CH2:1]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([O:22][C:23]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:1]([C:13]1[CH:14]=[C:15]2[C:16]([N:17]=[C:26]3[C:25](=[C:23]2[OH:22])[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 77014-DodecylanilineHCID 18686Ethyl cyclohexanoate

Product 1

HCID 178442815HCID 178442815, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Dodecylaniline (15.7 g) was dissolved in 100 mL of benzene and then 2-ethoxycarbonylcyclohexane (10.2 g) was added, followed by 0.20 g of p-toluenesulfonic acid. The reaction mixture was stirred for three days and then refluxed for 2 hours with the separation of H2O. The benzene was evaporated from this mixture, which was then dissolved in 100 mL of phenyl ether and refluxed for 45 minutes. At the end of this time the reaction mixture was allowed to cool and the precipitated product was filtered off. This crude product was purified by flash chromatography (20% ethyl acetate/CH2Cl2) and then recrystallized from 1,2-dichloroethane/methanol to give 1.31 g, mp 225°-226°.

Workup

  1. customThe benzene was evaporated from this mixture, which
  2. dissolutionwas then dissolved in 100 mL of phenyl ether
  3. temperaturerefluxed for 45 minutes
  4. temperatureto cool
  5. filtrationthe precipitated product was filtered off
  6. customThis crude product was purified by flash chromatography (20% ethyl acetate/CH2Cl2)
  7. customrecrystallized from 1,2-dichloroethane/methanol
  8. customto give 1.31 g, mp 225°-226°

Sources & evidence

ORD record
ord-4f0bcb9ef9e144f8b3e9ffbc7a97c647
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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