Hydrochloric Acid → HCID 66593839, compound

HRID 495165Notes

Reaction equation

HRID 495165 reaction equation
N1C=CC=CC=1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH3:18][C:19]1[CH:23]([CH3:24])[CH:22]=[C:21]([CH3:25])[C:20]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32].Cl>>[CH3:18][C:19]1[CH:23]([CH3:24])[CH:22]=[C:21]([CH3:25])[C:20]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 66593931HCID 66593931, compound

Product 1

HCID 66593839HCID 66593839, compoundYield 64%

Procedure

0.131 g (1.505 mmol) of pyridine and 0.316 g (1.656 mmol) of p-toluenesulfonyl chloride were added to 0.300 g (1.505 mmol) of 2-(2,3,5-trimethylcyclopenta-1,4-dienyl)phenylamine melted in 3 mL of MC, and then reacted at room temperature for 12 hours. 3 mL of 2 N HCl was added to the reaction product and strongly stirred for a few minutes. The organic layer was collected. The collected organic layer was neutralized with 3 mL of H2O without delay and dried over MgSO4. The product was filtered using a column chromatography with hexane/ethylacetate (v/v=3:1). The solvent contained in the purified product was dried in vacuum, thereby obtaining white solid (0.340 g, 64%).

Workup

  1. customreacted at room temperature for 12 hours
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. filtrationThe product was filtered
  5. customwas dried in vacuum

Sources & evidence

ORD record
ord-f882a6aa620a4093a9a7fc5e2f252d22
Source dataset
uspto-grants-2009_05
Patent number
US07538239B2

Reaction notes

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