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With tert-butyl N-tosyloxycarbamate at 20℃; for 36h; chemoselective reaction;
Multi-step reaction with 2 steps
1: 70 percent / nitration (method of Powell and Johnson in "Organic Syntheses"; Wiley: New York, 1955; Collect. Vol. 3, p. 449)
2: H2 / 5percent Pd/C / ethanol
Multi-step reaction with 2 steps
1: fuming nitric acid / 25 - 30 °C
2: iron; water
Multi-step reaction with 2 steps
1: nitric acid; acetic acid / 2 h / 20 °C
2: hydrogenchloride; tin; water / ethanol / 2 h / 70 °C
Multi-step reaction with 3 steps
1: AlCl3
2: 70 percent / nitration (method of Powell and Johnson in "Organic Syntheses"; Wiley: New York, 1955; Collect. Vol. 3, p. 449)
3: H2 / 5percent Pd/C / ethanol
Multi-step reaction with 3 steps
1: AlCl3
2: fuming nitric acid / 25 - 30 °C
3: iron; water
Stage #1: N-Benzyloxycarbonyl-L-proline With triethylamine In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With chloroformic acid ethyl ester In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: 2,4,6-triethylbenzenamine In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;
Stage #1: (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid With triethylamine In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With chloroformic acid ethyl ester In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: 2,4,6-triethylbenzenamine In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;
1-phenyl-2-(2,4,6-triethylphenyl)diazene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
With acetic acid at 20℃; Cooling;
General procedure for the coupling of anilines with nitrosobenzenes
General procedure: To the solution of the relevant 4-alkyl aniline derivative in glacial acetic acid (0.05 - 0.1 mol/L) is slowly added an equimolar amount of the respective nitrosobenzene at 20°C under water cooling. The reaction mixture is then stirred at room temperature until full conversion of the starting materials. Depending on the substitution pattern of the aniline derivative the coupling reaction takes hours to days until completion. The acetic acid is subsequently removed under reduced pressure. The residual crude product is adsorbed on silica gel and purified by column chromatography (usual solvent mixtures consist of 0.5 - 5 vol% diethyl ether in petrol ether). Solid diazenes are recrystallized afterwards.
5.2
2. Dissolve 2-bromo-3-benzyl bromide-benzaldehyde (3.6 mmol) in 35 mL of methanol.To this was added 2,4,6-triethylaniline (3.8 mmol).And adding acetic acid so that the pH of the solution is 5,After 9h at 25°C, the precipitate was collected by filtration to obtain Schiff base;
With acetic acid In methanol at 25℃; for 9h;
5.2
2. 2-bromo-3-benzyl bromide-benzaldehyde (3.6 mmol)Soluble in 35mL of methanol,To this was added 2,4,6-triethylaniline (3.8 mmol).And adding acetic acid so that the pH of the solution is 5,After 9h at 25°C, the precipitate was collected by filtration to obtain Schiff base;