Dimethylamine → N,N,2,4,6-Pentamethylbenzenamine

HRID 2229904Notes

Reaction equation

HRID 2229904 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[C:6]=1CCl>C1COCC1>[CH3:4][C:5]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[C:6]=1[N:2]([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 741082,4,6-Trimethylbenzyl chloride

Product 1

HCID 139365N,N,2,4,6-Pentamethylbenzenamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of THF (20 mL) and dimethylamine (20 mL, 40% wt in water) at 0° C. was added 2,4,6-trimethylbenzyl chloride (5 g, 29.64 mmol). The mixture was allowed to warm up to room temperature and stirred for 4 h before THF was evaporated and the aqueous residue was extracted with ether. The organic layer was worked up and concentrated as usual to give 2,4,6-trimethylphenyl-dimethylamine in quantitative yield. This compound was then nitrated and the resulted nitro compound reduced to the corresponding aniline as demonstrated in Example 14.

Workup

  1. customwas evaporated
  2. extractionthe aqueous residue was extracted with ether
  3. concentrationconcentrated as usual

Sources & evidence

ORD record
ord-4029ade288dc48a1b4f5ee5f9b0e13a5
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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