Hydrochloric Acid → HCID 66594030, compound

HRID 495166Notes

Reaction equation

HRID 495166 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:15][C:16]1[CH2:20][CH:19]=[C:18]([CH3:21])[C:17]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].Cl.C([O-])(O)=O.[Na+]>>[CH3:21][C:18]1[CH2:19][CH:20]=[C:16]([CH3:15])[C:17]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 665938692-(2,5-Dimethylcyclopenta-1,4-dien-1-yl)aniline

Product 1

HCID 66594030HCID 66594030, compoundYield 102.2%

Procedure

0.130 g (1.29 mmol) of triethylamine and 0.155 g (1.29 mmol) of pivaloyl chloride were added to 0.263 g (1.42 mmol) of 2-(2,5-dimethylcyclopenta-1,4-dienyl)phenylamine solution melted in 10 mL of MC solvent, and then reacted at room temperature for 1 hour. 5 mL of 2N HCl was added to the reaction product and strongly stirred for a few minutes. The organic layer was neutralized using 5 mL of NaHCO3, and the product was filtered using a column chromatography with a hexane/ethyl acetate (v/v, 10:1) solvent. The refined product was dried in vacuum to remove the solvent therein, thereby obtaining while solid (0.355 g, 93%).

Workup

  1. customreacted at room temperature for 1 hour
  2. filtrationthe product was filtered
  3. customThe refined product was dried in vacuum
  4. customto remove the solvent

Sources & evidence

ORD record
ord-4a68c135f17142be897c39d9ed98c03e
Source dataset
uspto-grants-2009_05
Patent number
US07538239B2

Reaction notes

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