Benzenesulfonyl chloride → 2-Pyrrolidinone, 5-(1-(methylethyl)thio)-1-(phenylsulfonyl)-

HRID 330502Notes

Reaction equation

HRID 330502 reaction equation
[CH:1]([S:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].C([Li])CCC.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.CCCCCC>[C:16]1([S:22]([N:9]2[CH:5]([S:4][CH:1]([CH3:3])[CH3:2])[CH2:6][CH2:7][C:8]2=[O:10])(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 198687005-Isopropylthio-pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 30781722-Pyrrolidinone, 5-(1-(methylethyl)thio)-1-(phenylsulfonyl)-Yield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 2.5 g of 5-isopropylthio-pyrrolidin-2-one in 130 cm3 of tetrahydrofuran, there is added at -70° to -65° C., 10.48 cm3 of a 1.5M solution of butyllithium in hexane. This is maintained for 20 minutes at this temperature, then 2.76 g of benzenesulphonyl chloride is added in 25 cm3 of tetrahydrofuran. After allowing to return to ambient temperature, concentrating under reduced pressure, taking up with water, filtering and drying, 2.15 g of the expected product is obtained. m.p., 91°-93° C., crystallized from ethanol.

Workup

  1. temperatureThis is maintained for 20 minutes at this temperature
  2. customto return to ambient temperature
  3. concentrationconcentrating under reduced pressure
  4. filtrationfiltering
  5. customdrying

Sources & evidence

ORD record
ord-844731310d2b48dca476d21709d2383b
Source dataset
uspto-grants-1990_01
Patent number
US04897414

Reaction notes

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