Pyridine → HCID 57656651, compound

HRID 658033Notes

Reaction equation

HRID 658033 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.C(OCC)(=O)C>C1COCC1.CN(C=O)C>[CH2:11]([O:18][C:19]1[CH:25]=[CH:24][CH:23]=[C:21]([NH:22][C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])[CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 928923-Benzyloxyaniline

Product 1

HCID 57656651HCID 57656651, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, after a solution of phenyl chloroformate (2.0 mL, 16 mmol) in THF (2.0 mL) was added dropwise to a solution of 3-benzyloxyaniline (3.7 g, 16 mmol) and pyridine (6.0 mL) in DMF (25 mL), the mixture was stirred at room temperature for 3 hours. Ethyl acetate (200 mL) was added thereto, and then the whole was washed with water (200 mL) twice and brine (200 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with diisopropyl ether, and dried under reduced pressure to give 3.7 g of the title reference compound as a white solid. (Yield 73%)

Workup

  1. washthe whole was washed with water (200 mL) twice
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. filtrationThe resulting solid was collected by filtration with diisopropyl ether
  5. customdried under reduced pressure
  6. customto give 3.7 g of the title reference compound as a white solid

Sources & evidence

ORD record
ord-984c5827ef1943e3ad2ac6494f2af070
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

Loading…