1,2-Dichlorobenzene → HCID 23141914, compound

HRID 32191Notes

Reaction equation

HRID 32191 reaction equation
[CH3:1][C:2]1[C:3]([C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH:10]=2)=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=CC=1Cl.Cl.Cl[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]Cl.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH:10]=2)=[C:4]([N:8]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 516892Sodium BicarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 231419913-Methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine

Product 1

HCID 23141914HCID 23141914, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
200 °C

Procedure

To a mixture of 3-methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine (663 mg, 2.72 mmol) produced in Example (71b) and 1,2-dichlorobenzene (3 mL) was added bis(2-chloroethyl)amine hydrochloride (632 mg, 3.54 mmol), followed by stirring for 5 hours and 50 minutes at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was passed through the reactor several times. The reaction mixture was cooled to room temperature, chloroform and saturated solution of sodium hydrogencarbonate were added, and the filtrate obtained by filtration through Celite was extracted with chloroform. The separated organic layer was washed with brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 625 mg of the title compound as a yellow solid.

Workup

  1. customDuring the reaction
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe filtrate obtained by filtration through Celite
  4. extractionwas extracted with chloroform
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c4f32b0c6a2840debe66d32a5ceb16b1
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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