Hydrochloric Acid → 2-(2-(2-Mesitylenesulfonyl)aminophenyl)-3-methyl-2-cyclopenten-1-one

HRID 495155Notes

Reaction equation

HRID 495155 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:14])[CH2:10][CH2:11][C:12]=1[CH3:13].N1C=CC=CC=1.[C:21]1([CH3:33])[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1[S:29](Cl)(=[O:31])=[O:30].Cl>C(Cl)Cl>[C:21]1([CH3:33])[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1[S:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:14])[CH2:10][CH2:11][C:12]=1[CH3:13])(=[O:30])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 130462-Mesitylenesulfonyl chlorideHCID 665938242-(2-Aminophenyl)-3-methylcyclopent-2-en-1-one

Product 1

HCID 665935232-(2-(2-Mesitylenesulfonyl)aminophenyl)-3-methyl-2-cyclopenten-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.500 g (2.67 mmol) of 2-(2-aminophenyl)-3-methyl-2-cyclopenten-1-one, 0.253 g (3.204 mmol) of pyridine, 0.584 g (2.67 mmol) of 2-mesitylenesulfonyl chloride), and 2 mL of M.C (methylene chloride) were loaded to a 20 mL vial, and then reacted for 12 hours. 10 mL of M.C and 4 mL of 2 N HCl were added to the reaction product. The resultant organic layer is collected and then dried over MgSO4 to remove water. The solvent contained in the dried product was removed using a rotary vacuum evaporator. The obtained solid was washed with 10 mL of diethyl ether and filtered using a glass filter. The filtered product was dried in vacuum to remove the solvent that had remained therein (0.790 g, 80%).

Workup

  1. customreacted for 12 hours
  2. customThe resultant organic layer is collected
  3. dry with materialdried over MgSO4
  4. customto remove water
  5. customwas removed
  6. customa rotary vacuum evaporator
  7. washThe obtained solid was washed with 10 mL of diethyl ether
  8. filtrationfiltered
  9. filtrationfilter
  10. customThe filtered product was dried in vacuum
  11. customto remove the solvent that

Sources & evidence

ORD record
ord-7250fab07000496c97034d8f5dd6c609
Source dataset
uspto-grants-2009_05
Patent number
US07538239B2

Reaction notes

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