Hydrochloric Acid → HCID 66594030, compound

HRID 492098Notes

Reaction equation

HRID 492098 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>>[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

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 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 dissolved in 10 mL of an MC solvent and then reacted at room temperature for one hour. 5 mL of 2N HCl was added to the reaction solution and then strongly stirred for a few minutes. The organic layer was collected and then neutralized by 5 mL of NaHCO3 saturated aqueous solution. The resultant product was purified through a column chromatography using a solvent of hexane/ethyl acetate (v/v, 10:1), and then dried in vacuum to remove the solvent therein, thereby obtaining white solid (0.355 g, 93%).

Workup

  1. dissolutiondissolved in 10 mL of an MC solvent
  2. customreacted at room temperature for one hour
  3. customThe organic layer was collected
  4. customThe resultant product was purified through a column chromatography
  5. customdried in vacuum
  6. customto remove the solvent

Sources & evidence

ORD record
ord-33cbe7eead4b49f3bcc99e4289d94fe6
Source dataset
uspto-grants-2009_05
Patent number
US07531608B2

Reaction notes

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