Hydrochloric Acid → HCID 19857641, compound

HRID 2073664Notes

Reaction equation

HRID 2073664 reaction equation
[Br:1]Br.Cl.[CH:4]([C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[C:8]=1[NH2:9])([CH3:6])[CH3:5].Cl>C1CCCCC1>[BrH:1].[Br:1][C:12]1[CH:13]=[C:7]([CH:4]([CH3:6])[CH3:5])[C:8]([NH2:9])=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24408BromineHCID 111834762,6-Di(propan-2-yl)aniline--hydrogen chloride (1/1)

Product 1

HCID 19857641HCID 19857641, compoundYield 169.3%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
10 °C

Procedure

19.1 g of bromine are added dropwise at 70° C. over 2 hours to a suspension of 24.1 g of 2,6-diisopropylaniline hydrochloride in 150 ml of cyclohexane. The hydrogen chloride evolved in the course of this addition escapes continuously. The reaction mixture is cooled to 10° C. and then filtered. The filter residue is washed with cyclohexane and dried at 40° C. under vacuum, affording 34.1 g of 4-bromo-2,6-diisopropylaniline hydrobromide (99.9% of theory) in the form of yellow crystals of 98.7% purity and having a melting point of 234°-235° C. (compound 1).

Workup

  1. filtrationfiltered
  2. washThe filter residue is washed with cyclohexane
  3. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-76f9ba5c09664218a24519271b791d10
Source dataset
uspto-grants-1990_04
Patent number
US04918230

Reaction notes

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