Potassium Carbonate → Ethyl {[4-(adamantan-1-yl)phenyl]amino}(oxo)acetate

HRID 1626772Notes

Reaction equation

HRID 1626772 reaction equation
[C:1]12([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:25](=[O:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1COCC1>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([NH:15][C:25](=[O:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:16][CH:17]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20884Ethoxalyl chlorideHCID 5985444-(Adamantan-1-yl)aniline

Product 1

HCID 66680869Ethyl {[4-(adamantan-1-yl)phenyl]amino}(oxo)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 mL of THF was added to 400 mg (1.76 mmol) of 4-(adamantan-1-yl)aniline, after which 292 mg (2.11 mmol) of potassium carbonate was added. 291 mg (1.94 mmol) of ethyl chloroglyoxylate was added at 0° C., and the mixture was stirred at room temperature for 2 hours. Thereafter, the mixture was filtered using silica gel, and the filtrate was condensed. The obtained crude product was then separated and purified by silica gel column chromatography, thereby quantitatively giving ethyl {[4-(adamantan-1-yl)phenyl]amino}(oxo)acetate.

Workup

  1. filtrationThereafter, the mixture was filtered
  2. customcondensed
  3. customThe obtained crude product
  4. customwas then separated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-72ec551851394bd39c46375c0ec4e320
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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