Chlorosuccinimide → 2-Chloro-3-(3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one

HRID 1977597Notes

Reaction equation

HRID 1977597 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[NH:10][C:11]2[CH2:15][CH2:14][C:13](=[O:16])[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:22]N1C(=O)CCC1=O>C(O)C.O.C(OCC)(=O)C>[Cl:22][C:12]1[C:13](=[O:16])[CH2:14][CH2:15][C:11]=1[NH:10][C:9]1[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 155213543-(3-Cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one

Product 1

HCID 219944182-Chloro-3-(3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-oneYield 82.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

To a solution 0.49 g (1.69 mmole) of the 3-(3-cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one produced in Example 1(3) in 5 ml of an ethanol-water (9:1) solution was added 0.25 g (1.86 mmole) of N-chlorosuccinimide. The mixture was stirred at room temperature for 1.5 hours. After the reaction, the solvent was removed in vacuo. Next, the residue obtained was diluted with 100 ml of ethyl acetate and the solution was successively washed with a saturated sodium hydrogencarbonate solution and brine. The organic solution was dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo to obtain a crude product as a black oil. The crude product obtained here was purified by flash chromatography. The solvent was removed and the residue dried in vacuo to obtain the title compound 0.45 g (yield 82.5%) as a light pink solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed in vacuo
  3. customNext, the residue obtained
  4. washthe solution was successively washed with a saturated sodium hydrogencarbonate solution and brine
  5. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customto obtain a crude product as a black oil
  8. customThe crude product obtained here
  9. customwas purified by flash chromatography
  10. customThe solvent was removed
  11. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-abc60002b7d646c591df7426801ba9a2
Source dataset
uspto-grants-2001_05
Patent number
US06235736B1

Reaction notes

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