Hydrochloric Acid → 4-tert-Octyl-2-nitrobenzene Diazonium Chloride

HRID 4715Notes

Reaction equation

HRID 4715 reaction equation
[C:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].[ClH:19].[N:20]([O-])=O.[Na+]>C1(C)C=CC=CC=1.O>[Cl-:19].[C:1]([C:9]1[CH:15]=[CH:14][C:12]([N+:13]#[N:20])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 141221784-Tert-octyl-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 141221794-tert-Octyl-2-nitrobenzene Diazonium Chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
38 °C

Procedure

In a 100-ml flask fitted with a stirrer and thermometer, 15.0 grams (0.06 mole) of 4-tert-octyl-2-nitroaniline is suspended in 20 ml of toluene. To this is added at 25° C. 17.3 grams (0.18 mole) of concentrated hydrochloric acid. The suspension is stirred at 38° C. for 1 hour followed by the addition of 6 ml of water. The mixture becomes thick as the corresponding hydrochloride salt crystallized as a granular precipitate. The mixture is cooled to 0° C. and diazotized by the addition over a period of 30 minutes of 4.3 grams (0.062 mole) of sodium nitrite in 6 ml of water keeping the temperature at -5° C. to -2° C. The mixture is stirred at -2° C. for 1 hour. Two phases occur. The combined phases contain the desired diazonium chloride and are used as is.

Workup

  1. customIn a 100-ml flask fitted with a stirrer
  2. additionTo this is added at 25° C
  3. customcrystallized as a granular precipitate
  4. temperatureThe mixture is cooled to 0° C.
  5. stirringThe mixture is stirred at -2° C. for 1 hour

Sources & evidence

ORD record
ord-40e6f1d5d42a4cd08132d0bdb6e46fe3
Source dataset
uspto-grants-1988_02
Patent number
US04727158

Reaction notes

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