Pyridine → HCID 67344250, compound

HRID 1673479Notes

Reaction equation

HRID 1673479 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10](Cl)=[O:11].[NH2:18][C:19]1[CH:31]=[C:30]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10]([NH:18][C:19]1[CH:31]=[C:30]([CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:11]

Participants

6

Reactant 4

HCID 1049PyridineHCID 783922,6-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 67344250HCID 67344250, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.061 mL of pyridine and 0.086 mL of 2,6-dichlorobenzoyl chloride were added to 3.0 mL of toluene solution containing 0.15 g of tert-butyl 2-amino-4-phenethylbenzoate at room temperature sequentially, and the resulting mixture was heated to reflux for 8 hours. The reaction mixture was cooled to room temperature and a saturated sodium hydrogen carbonate aqueous solution was added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid, aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1] to obtain tert-butyl 2-(2,6-dichlorobenzamido)-4-phenethylbenzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 8 hours
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with 10% citric acid, aqueous solution
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1]

Sources & evidence

ORD record
ord-0ad6d2763ae14b92b1cbccf06d3e2b7d
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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