2-Naphthalenesulfonyl chloride → HCID 14424883, compound

HRID 373714Notes

Reaction equation

HRID 373714 reaction equation
C([Li])CCC.[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[S:22](Cl)(=[O:24])=[O:23]>CCCCCC.O1CCCC1>[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[S:22]([N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])(=[O:23])=[O:24]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 120252-PyrrolidoneHCID 178418339Butyllithium

Product 1

HCID 14424883HCID 14424883, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

15.6 cm3 of a 1.6M solution of butyllithium in hexane is added to 2.13 g of 2-pyrrolidinone in solution in 80 cm3 of tetrahydrofuran, cooled to -10° C., maintaining the temperature between -5° C. and +5° C. After agitation at -5° C. for 25 minutes, 6.12 g of beta-naphthalene-sulphonyl chloride is added, without exceeding 0° C. The whole is then left to return to ambient temperature. The solvent is evaporated off under reduced pressure, the residue is taken up in ethyl acetate, and the lithium chloride is filtered off and after evaporating under reduced pressure, the residue is taken up in water and filtered. Finally after crystallization from isopropanol, 4 g of expected product is obtained.

Workup

  1. temperaturemaintaining the temperature between -5° C. and +5° C
  2. customwithout exceeding 0° C
  3. waitThe whole is then left
  4. customto return to ambient temperature
  5. customThe solvent is evaporated off under reduced pressure
  6. filtrationthe lithium chloride is filtered off
  7. customafter evaporating under reduced pressure
  8. filtrationfiltered
  9. customFinally after crystallization from isopropanol

Sources & evidence

ORD record
ord-4ccb95a9852e4911b328b171bc72df86
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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