2,4,6-Trimethylaniline → HCID 58896535, compound

HRID 2235536Notes

Reaction equation

HRID 2235536 reaction equation
[CH2:1]([N:8]([CH2:20][CH2:21][CH3:22])[C:9]1[C:14]2[N:15]([CH3:19])[C:16](Cl)=[N:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH3:32])[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:24]=1[NH2:31]>C(OCC)(=O)C>[CH2:1]([N:8]([CH2:20][CH2:21][CH3:22])[C:9]1[C:14]2[N:15]([CH3:19])[C:16]([NH:31][C:24]3[C:25]([CH3:30])=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=3[CH3:32])=[N:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 86612997HCID 86612997, compound

Product 1

HCID 58896535HCID 58896535, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.56 g (1.8 mmol) of N7-benzyl-2-chloro-1-methyl-N7-propyl-1H-benzimidazol-7-amine in 0.75 mL (5.4 mmol) of mesityl amine was heated to 130° C. After stirring for 24 h, the mixture was dissolved in ethyl acetate and washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to give a tan solid. The solid thus obtained was purified by flash chromatography eluting with a 1.3% methanol/dichloromethane mixture to give 0.59 g (80%) of the title compound as a cream colored solid.

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a tan solid
  6. customThe solid thus obtained
  7. customwas purified by flash chromatography
  8. washeluting with a 1.3% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-fb67382c2c2b4c418ad6a628052c39e0
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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