Potassium Iodide → HCID 20512441, compound

HRID 894582Notes

Reaction equation

HRID 894582 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].[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17].[I-].[K+]>C(O)(C)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:17][C:16]1[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:15]=1[CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 68962,6-DimethylanilineHCID 13674776HCID 13674776, compound

Product 1

HCID 20512441HCID 20512441, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 86 g (0.435 moles) of N-(β-chloropropyl)-2,6-dimethyl-aniline, prepared as described in point (a) above, 110 ml (107.4 g, 0.88 moles) of 2,6-dimethylaniline and 4.2 g (25 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 80° C., 300 ml of isopropanol are added, the resulting mixture is allowed to cool to room temperature under stirring, and then allowed to stand overnight. The separated precipitate is filtered off, washed with cold (+5° C.) isopropanol and dried. 67.1 g (42.4%) of crude 1,2-bis(2',6'-dimethylphenyl-amino)-propane hydrochloride (fraction A) are obtained. The filtrate is admixed with 200 ml of 20% aqueous hydrochloric acid, and the mixture is allowed to stand for 24 hours. The separated precipitate is filtered off, washed with water and dried. In this way further 48 g (34.6%) of crude 1,2-bis(2',6'-dimethylphenyl-amino)propane hydrochloride (fraction B) are obtained, thus the total yield is 83.0%. Fractions A and B are combined, dissolved in a mixture of 500 ml of dimethyl formamide and 250 ml of water, and the solution is rendered alkaline (pH=10) with 10 n aqueous sodium hydroxide solution. The solution is admixed with 2 liters of water, the separated precipitate is filtered off, washed with water, and dried. 87.15 g (70.9%) of 1,2-bis(2',6'-dimethylphenyl-amino)-propane (m.p.: 52°-55° C.) are obtained. This product is sufficiently pure to apply it directly in the next step.

Workup

  1. customprepared
  2. temperatureto cool to room temperature
  3. stirringunder stirring
  4. waitto stand overnight
  5. filtrationThe separated precipitate is filtered off
  6. washwashed with cold (+5° C.) isopropanol
  7. customdried

Sources & evidence

ORD record
ord-aeb33aecfcb54a1b9dc2fb967483c797
Source dataset
uspto-grants-1981_08
Patent number
US04284642

Reaction notes

Loading…