2,4,6-Trimethylaniline → Benzenamine, 2,4,6-trimethyl-, hydrochloride (1:1)

HRID 894591Notes

Reaction equation

HRID 894591 reaction equation
[Cl:1]C(C)C[NH:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13].CC1C=C(C)C=C(C)C=1N>[I-].[K+].C(OCC)C>[ClH:1].[CH3:13][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[C:5]=1[NH2:4]

Participants

5

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 20512433HCID 20512433, compound

Product 1

HCID 5284471Benzenamine, 2,4,6-trimethyl-, hydrochloride (1:1)Yield 93.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

32.75 g (0.155 moles) of N-(β-chloropropyl)-2,4,6-trimethyl-aniline, prepared as indicated in point (b) above, are reacted with 41.8 g (0.31 moles) of 2,4,6-trimethylaniline in the presence of 1.0 g (6 mmoles) of potassium iodide as described in Example 3, Method (b), point (b). The resulting mixture is admixed with 50 ml of diethyl ether, the separated precipitate is filtered off, washed with diethyl ether and dried. 24.8 g (46.6%) of 2,4,6-trimethylaniline hydrochloride are obtained. The filtrate is acidified with isopropanolic hydrochloric acid (acid content: about 15 g/100 ml), and the resulting mixture is maintained at 0° to +5° for 2 hours. The separated precipitate is filtered off, washed with cold isopropanol, and dried. 50.3 g (84.8%) of 1,2-bis(2',4',6'-trimethylphenyl-amino)-propane dihydrochloride are obtained; m.p.: 172°-173° C. The base is liberated from this salt as described in Example 3, Method (b), point (b), and is separated from the reaction mixture by chloroform extraction.

Workup

  1. filtrationthe separated precipitate is filtered off
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-83d935dc5e384d988c1d09b21300c271
Source dataset
uspto-grants-1981_08
Patent number
US04284642

Reaction notes

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