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

HRID 1164447Notes

Reaction equation

HRID 1164447 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-trimethyl-aniline 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-de23ea10ee8249e0b1d9f119d5f35b34
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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