Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-5-ethoxypyrrolidin-2-one

HRID 1761883Notes

Reaction equation

HRID 1761883 reaction equation
[CH2:1]([O:3][CH:4]1[NH:8][C:7](=[O:9])[CH2:6][CH2:5]1)[CH3:2].C([Li])CCC.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1.CCCCCC>[C:15]1([S:21]([N:8]2[CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][C:7]2=[O:9])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 35805555-Ethoxy-2-pyrrolidinoneHCID 178418339Butyllithium

Product 1

HCID 1830901-(Benzenesulfonyl)-5-ethoxypyrrolidin-2-oneYield 29.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

To 4.5 g of 5-ethoxypyrrolidin-2-one dissolved in 140 cm3 of anhydrous tetrahydrofuran, 21.8 cm3 of butyl-lithium in hexane (1.6M) is added drop by drop under an inert atmosphere, while cooling to about -10° C. After 45 minutes, 6.15 g of benzenesulphonyl chloride in tetrahydrofuran is added, and the whole is kept at -10° C. under agitation for 2 hours. It is then returned to ambient temperature, and the residue, after concentrating under reduced pressure, is taken up in 100° ethanol. By cooling and under agitation, the product precipitates, and is then filtered, washed abundantly with water, dried, and 2.8 g of the expected product is obtained after crystallizing from isopropanol, m.p. 112°-113° C.

Workup

  1. waitthe whole is kept at -10° C. under agitation for 2 hours
  2. customis then returned to ambient temperature
  3. concentrationthe residue, after concentrating under reduced pressure
  4. customis taken up in 100°
  5. temperatureBy cooling and under agitation
  6. customthe product precipitates
  7. filtrationis then filtered
  8. washwashed abundantly with water
  9. customdried

Sources & evidence

ORD record
ord-acbb66a79af143b8b1015149af431b35
Source dataset
uspto-grants-1989_05
Patent number
US04829079

Reaction notes

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