Benzenesulfonyl chloride → 1-Benzenesulphonyl-2-oxo-5-propylthio-pyrrolidine

HRID 330504Notes

Reaction equation

HRID 330504 reaction equation
[CH2:1]([S:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1)[CH2:2][CH3:3].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][CH2:1][CH2:2][CH3:3])[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 198687015-Propylthio-pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 198687031-Benzenesulphonyl-2-oxo-5-propylthio-pyrrolidineYield 34.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 2.3 g of 5-propylthio-pyrrolidin-2-one in solution in 120 cm3 of tetrahydrofuran, there is added at -70° C./-65° C., 9.6 cm3 of a 1.5M solution of butyllithium in hexane. After 20 minutes at this temperature, 2.55 g of benzenesulphonyl chloride is added in 20 cm3 of tetrahydrofuran. After allowing to return slowly to ambient temperature, concentrating and chromatographing on silica (eluent: hexane-ethyl acetate, 3-7), 1.5 g of the expected product is obtained. m.p. 49°-51° C. crystallized from isopropyl ether.

Workup

  1. customto return slowly to ambient temperature
  2. concentrationconcentrating

Sources & evidence

ORD record
ord-d11a6d1e80bf41e198a7757cd8f48106
Source dataset
uspto-grants-1990_01
Patent number
US04897414

Reaction notes

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