Potassium Iodide → HCID 20512453, compound

HRID 894604Notes

Reaction equation

HRID 894604 reaction equation
[Cl:1][CH:2]([CH3:13])[CH2:3][NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12].[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.[I-].[K+]>C(OCC)(=O)C>[ClH:1].[CH3:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=1[NH:4][CH2:3][CH:2]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([Cl:14])=[CH:16][CH:17]=1)[CH3:13]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 78124-ChloroanilineHCID 13674776HCID 13674776, compound

Product 1

HCID 20512453HCID 20512453, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 28.2 g (0.143 moles) of N-(β-chloropropyl)-2,6-dimethylaniline, prepared as described in Example 3, Method (b), point (a), 36.4 g (0.285 moles) of 4-chloroaniline and 1.6 g (10 mmoles) of potassium iodide is stirred at 140° to 145° C. for 3 hours under nitrogen atmosphere. The mixture is allowed to cool to about 60° C., and 30 ml of ethyl acetate are added. The mixture is cooled to room temperature, and the separated precipitate is filtered off, washed with ethyl acetate and dried. 14.0 g of 1-(2',6'-dimethyl-phenylamino)-2-(4'-chlorophenyl-amino)-propane hydrochloride (fraction A) are obtained. The filtrate is acidified with isopropanolic hydrochloric acid (acid content: about 15 g/100 ml), the separated precipitate is filtered off, washed with isopropanol and dried. 28.8 g of the same compound (fraction B) are obtained. Fractions A and B are combined, triturated with 100 ml of water, filtered, washed with water, dried, and the resulting solid, weighing 25.7 g, is recrystallized from methanol. 21.4 g (46.0%) of pure 1-(2',6'-dimethylphenylamino)-2-(4'-chlorophenyl-amino)-propane hydrochloride are obtained; m.p.: 170°-176° C. This salt is converted to the free base as described in Example 3, Method (b), point (b), and the base is separated by extracting the reaction mixture with chloroform.

Workup

  1. customprepared
  2. temperatureThe mixture is cooled to room temperature
  3. filtrationthe separated precipitate is filtered off
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-c24bd872949c404da259c86fa88ee5e0
Source dataset
uspto-grants-1981_08
Patent number
US04284642

Reaction notes

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