Toluene → HCID 86597667, compound

HRID 1951661Notes

Reaction equation

HRID 1951661 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([C:25]([CH3:30])([CH3:29])[C:26](Cl)=[O:27])[CH:21]=[C:22]([Cl:24])[CH:23]=1.C1(C)C=CC=CC=1>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:9])[C:26](=[O:27])[C:25]([C:20]2[CH:19]=[C:18]([Cl:17])[CH:23]=[C:22]([Cl:24])[CH:21]=2)([CH3:30])[CH3:29])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 115289412-(3,5-Dichloro-phenyl)-2-methyl-propionyl chlorideHCID 23502811[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 86597667HCID 86597667, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1.20 g (4.74 mmol) [6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine and 1.43 g (5.68 mmol) 2-(3,5-dichloro-phenyl)-2-methyl-propionyl chloride in 20 ml toluene 1.27 g (10.42 mmol) 4-dimethylaminopyridine was added and the resulting solution stirred at 120° for 48 h. After cooling to ambient temperature, the solution was poured into 100 ml 0.5 N NaHCO3-solution and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, hexanes/ethyl acetate 4:1) to give 1.90 g (85%) of the title compound as a white solid.

Workup

  1. extractionextracted three times with 50 ml CH2Cl2
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash-chromatography (SiO2, hexanes/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-f07caca19213437a8bd350e343a0be6d
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

Loading…