3,4-Dimethylaniline → HCID 178426384, compound

HRID 1515064Notes

Reaction equation

HRID 1515064 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18](=O)[C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[CH3:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[CH3:32])[NH2:28].C(N(C(C)C)CC)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:24][C:25]1[CH:26]=[C:27](/[N:28]=[C:18](/[C:16]2[CH:15]=[CH:14][C:12]3[N:13]=[C:9]([C:3]4[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[NH:10][C:11]=3[CH:17]=2)\[C:19]([F:22])([F:20])[F:21])[CH:29]=[CH:30][C:31]=1[CH3:32]

Participants

6

Reactant 3

HCID 72483,4-DimethylanilineHCID 81531DiisopropylethylamineHCID 66965746HCID 66965746, compound

Product 1

HCID 178426384HCID 178426384, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[2-(2,6-dimethylphenyl)-3H-benzoimidazol-5-yl]-2,2,2-trifluoro-ethanone (710 mg), 3,4-dimethylaniline (150 mg) and diisopropylethylamine (150 mg) in methylene chloride (15 mL) was added dropwise 1.1 mL of a 1.0M solution of TiCl4 in methylene chloride. The mixture was stirred at ambient temperature for 10 min then was washed with NaHCO3 solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 10% EtOAc/methylene chloride as eluent to give (3,4-dimethyl-phenyl)-[1-[2-(2,6-dimethylphenyl)-3H-benzoimidazol-5-yl]-2,2,2-trifluoroeth-(Z)-ylidene]-amine as an oil. This was used directly in the next reaction.

Workup

  1. washthen was washed with NaHCO3 solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e84ace4057b546949eaaa116904d4fdd
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…