Benzylamine → HCID 89975793, compound

HRID 716165Notes

Reaction equation

HRID 716165 reaction equation
Br[CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>O.C(OCC)(=O)C.C(#N)C>[CH2:8]([N:15]([CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7])[C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([CH3:22])=[CH:24][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 134054-Methylbenzoyl ChlorideHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 89975793HCID 89975793, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 10 g of 3-bromo-2-oxooxolane, 6.6 g of benzylamine, 21 g of potassium carbonate and 200 mL of acetonitrile was stirred at 70° C. for 1 hour 30 minutes. Thereafter, 7.9 mL of 4-methylbenzoyl chloride was added dropwise to the reaction mixture at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 2 hours. Thereafter, 400 mL of ethyl acetate and 200 mL of water were added to the reaction mixture. The organic layer was fractionated. The obtained organic layer was successively washed with 100 mL of water and 100 mL of a saturated sodium chloride aqueous solution, and it was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then dissolved in 100 mL of ethyl acetate under heating. After that, 100 mL of hexane was added dropwise to the reaction mixture at 50° C. A solid was collected by filtration, so as to obtain 11.2 g of N-benzyl-4-methyl-N-(2-oxooxolan-3-yl)benzamide.

Workup

  1. stirringthe obtained mixture was then stirred at room temperature for 2 hours
  2. washThe obtained organic layer was successively washed with 100 mL of water and 100 mL of a saturated sodium chloride aqueous solution, and it
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. dissolutionthe obtained residue was then dissolved in 100 mL of ethyl acetate
  6. temperatureunder heating
  7. additionAfter that, 100 mL of hexane was added dropwise to the reaction mixture at 50° C
  8. filtrationA solid was collected by filtration

Sources & evidence

ORD record
ord-0263ad0a8f41471ebe5b884499136be9
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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