2-Pyrrolidone → HCID 19811001, compound

HRID 1090106Notes

Reaction equation

HRID 1090106 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([S:15](S(Cl)(=O)=O)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1>CCCCCC.O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([S:15]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 120252-PyrrolidoneHCID 19914545HCID 19914545, compound

Product 1

HCID 19811001HCID 19811001, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-25 °C

Procedure

15.75 cm3 of a 1.6M solution of M-butyllithium in hexane is added to 2.22 g of 2-pyrrolidinone in solution in 80 cm3 of tetrahydrofuran and cooled to -25° C., the temperature being maintained between -25° C. and -20° C. After agitation for 30 minutes at -25° C., a solution of 5.40 g of 3-methoxybenzenesulphonyl sulphonyl chloride [J. Chem. Soc. P.T.2., 579 (1982)] in 40 cm3 of tetrahydrofuran is poured drop by drop into the mixture, operating between -25° C. and -20° C. After agitation for 30 minutes at -25° C., the whole is allowed to return to ambient temperature. The solvent is evaporated under reduced pressure; the residue is taken up in water, filtered and crystallized from isopropanol. 3.5 g of expected product is obtained.

Workup

  1. temperaturethe temperature being maintained between -25° C. and -20° C
  2. customoperating between -25° C. and -20° C
  3. waitAfter agitation for 30 minutes at -25° C.
  4. customto return to ambient temperature
  5. customThe solvent is evaporated under reduced pressure
  6. filtrationfiltered
  7. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-fc1a45abd7d1417993026eafa8612a8e
Source dataset
uspto-grants-1992_01
Patent number
US05081130

Reaction notes

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