2-Pyrrolidone → HCID 19811001, compound

HRID 373713Notes

Reaction equation

HRID 373713 reaction equation
[Li+].CCC[CH2-].[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>CCCCCC.O1CCCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([S:20]([N:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 61028n-Butyl lithiumHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 19811001HCID 19811001, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-25 °C

Procedure

15.75 cm3 of a 1.6M solution of N-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 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-56a1815db7064dbe8fb35830a86fa582
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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