2-Pyrrolidone → 4-(Dimethylamino)benzenesulphonyl-2-pyrrolidinone

HRID 373710Notes

Reaction equation

HRID 373710 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH3:9][N:10]([CH3:21])[C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>O1CCOCC1>[CH3:9][N:10]([CH3:21])[C:11]1[CH:12]=[CH:13][C:14]([S:17]([N:3]2[CH2:7][CH2:6][CH2:5][C:4]2=[O:8])(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 125069434-(Dimethylamino)benzene-1-sulfonyl chloride

Product 1

HCID 100615704-(Dimethylamino)benzenesulphonyl-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3.44 g of sodium hydride (at 55-60% in oil) is added to a solution comprising 6.11 g of 2-pyrrolidinone and 200 cm3 of dioxan, with agitation for one hour at ambient temperature. 15.76 cm3 of 4-dimethylaminobenzenesulphonyl chloride [Beritche 43, 3038 (1910)] in solution in 250 cm3 of dioxan is added drop by drop, with agitation for one hour at ambient temperature. The sodium chloride is filtered off on celite, the dioxan is evaporated off under reduced pressure, the residue is crystallized from acetone and 3.90 g of expected product is obtained.

Workup

  1. waitwith agitation for one hour at ambient temperature
  2. filtrationThe sodium chloride is filtered off on celite
  3. customthe dioxan is evaporated off under reduced pressure
  4. customthe residue is crystallized from acetone

Sources & evidence

ORD record
ord-878c89a77ddb4707ba8bc175ed630132
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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