2,4,6-Trimethylaniline → HCID 11154972, compound

HRID 2235551Notes

Reaction equation

HRID 2235551 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8](Cl)[N:7]([CH3:12])[C:6]=2[C:5]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1.[C:20]1([CH3:29])[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[NH2:28]>C(OCC)(=O)C>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([NH:28][C:21]3[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:20]=3[CH3:29])[N:7]([CH3:12])[C:6]=2[C:5]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 68581147HCID 68581147, compound

Product 1

HCID 11154972HCID 11154972, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-2-chloro-1-methyl-N,N-dipropyl-1H-benzimidazol-7-amine (220 mg, 0.638 mmol) and mesityl amine (1.79 ml, 12.8 mmol) was heated at 120° C. for 60 h. The mixture was dissolved in ethyl acetate and washed with saturated sodium bicarbonate in water, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting 5% n-hexane/ethyl acetate to afford the title compound.

Workup

  1. washwashed with saturated sodium bicarbonate in water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography
  5. washeluting 5% n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-d96a7254696345d0be7c9c6950e86221
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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