2-Pyrrolidone → HCID 19810994, compound

HRID 373711Notes

Reaction equation

HRID 373711 reaction equation
C([Li])CCC.[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CCCCCC.O1CCCC1>[CH3:12][S:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([N:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 111387314-(Methylsulfanyl)benzene-1-sulfonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 19810994HCID 19810994, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

16.95 cm3 of a 1.6M solution of n-butyllithium in n-hexane is added drop by drop to 2.29 g of 2-pyrrolidinone in solution in 160 cm3 of anhydrous tetrahydrofuran cooled to -30° C., maintaining the temperature at -30° C. After agitation for 30 minutes, the mixture is poured drop by drop into a solution containing 6 g of 4-methylthio-benzenesulphonyl chloride [J. Chem. Soc. (1948) 604] in 10 cm3 of tetrahydrofuran, operating between -30° and -25° C. The whole is left to return to ambient temperature. The solvent is evaporated off under reduced pressure, the residue is taken up in water and the solid is filtered off. After crystallization from isopropanol, 3.80 g of expected product is obtained.

Workup

  1. temperaturemaintaining the temperature at -30° C
  2. additionthe mixture is poured drop by drop into a solution
  3. customoperating between -30° and -25° C
  4. waitThe whole is left
  5. customto return to ambient temperature
  6. customThe solvent is evaporated off under reduced pressure
  7. filtrationthe solid is filtered off
  8. customAfter crystallization from isopropanol

Sources & evidence

ORD record
ord-3ba724774ccc4ece833822b080c45e1f
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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