Pyridine → HCID 67342146, compound

HRID 1673483Notes

Reaction equation

HRID 1673483 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].C1(C)C=CC=CC=1.[NH2:25][C:26]1[CH:38]=[C:37]([O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>O>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10]([NH:25][C:26]1[CH:38]=[C:37]([O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[O:11]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 1140TolueneHCID 783922,6-Dichlorobenzoyl chloride2×HCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Product 1

HCID 67342146HCID 67342146, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.089 mL of pyridine and 0.11 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-phenoxybenzoate at room temperature sequentially, and the resulting mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and 0.021 mL of pyridine and 0.037 mL of 2,6-dichlorobenzoyl chloride were added sequentially and heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and water was added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate 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-phenoxybenzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureheated
  4. temperatureto reflux for 4 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  9. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

Sources & evidence

ORD record
ord-5b5a81b4092d4e97b6c9411d3e83d0a8
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

Loading…