Pyridine → HCID 86634615, compound

HRID 1673481Notes

Reaction equation

HRID 1673481 reaction equation
N1C=CC=[CH:3][CH:2]=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]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])(C)C)=[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]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][CH2:31][CH2:34][CH2:2][CH3:3])=[O:29])=[O:11]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 1140TolueneHCID 783922,6-Dichlorobenzoyl chloride2×HCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 86634615HCID 86634615, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.090 mL of pyridine and 0.12 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-phenylbenzoate at room temperature sequentially, and the resulting mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and 0.023 mL of pyridine and 0.040 mL of 2,6-dichlorobenzoyl chloride were added sequentially and the resulting mixture was heated to reflux for 2 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 chloride aqueous solution, 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 herb-butyl 2-(2,6-dichlorobenzamido)-4-phenylbenzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux for 2 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 chloride aqueous solution
  9. customthe solvent was evaporated under reduced pressure
  10. 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-4413a7c8eb124c7c932ca7907dd6a494
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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