p-Toluenesulfonic acid → HCID 85040011, compound

HRID 2287481Notes

Reaction equation

HRID 2287481 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[CH:12]1([NH:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N+:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O-:19])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 248344-EthoxybenzaldehydeHCID 72935Cyclohexylhydroxylamine

Product 1

HCID 85040011HCID 85040011, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-ethoxybenzaldehyde (6.62 g, 44.1 mmol) in 200 mL of benzene was refluxed with N-cyclohexylhydroxylamine (6.61 g, 57.4 mmol) in the presence of p-toluenesulfonic acid (0.8 g, 4 mmol) for 72 h. After rotary evaporation, the residue was purified by recrystallization from hexanes and ethylene glycol dimethyl ether (100 mL, 3: 1, v:v) to give the title compound (9.2 g, 84% yield) as a solid, m.p. 124.0° C.

Workup

  1. customAfter rotary evaporation
  2. customthe residue was purified by recrystallization from hexanes and ethylene glycol dimethyl ether (100 mL, 3: 1, v:v)

Sources & evidence

ORD record
ord-cb543e870e4e45f0b0519def7274e08b
Source dataset
uspto-grants-2000_07
Patent number
US06083989

Reaction notes

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