Lawesson's reagent → HCID 10018426, compound

HRID 2247824Notes

Reaction equation

HRID 2247824 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=O)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[S:30])(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 104472822-Pyrrolidinone, 1-[[4-(diethylamino)phenyl]sulfonyl]-

Product 1

HCID 10018426HCID 10018426, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture comprising 9 g of 1-[4-(diethylamino)benzenesulphonyl]-2-pyrrolidinone, prepared as in Example 2 of the European Patent published under No. 0,033,578, and 6.15 g of Lawesson reagent (or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide) in 180 cm3 of toluene is heated to reflux for 1 hour. The mixture is allowed to return to room temperature and is evaporated to dryness, the residue is taken up in 200 cm3 of chloroform and the resulting mixture is dried, filtered on celite and evaporated to dryness. 3.6 g of crude product (m.p. 170°-180° C.) are recovered, which product is chromatographed on silica (eluant: ethyl acetate/n-hexane, 2:1) and the residue is then crystallized in ethanol. 2.4 g of expected product are obtained. M.p. 183°-184° C.

Workup

  1. temperatureto reflux for 1 hour
  2. customto return to room temperature
  3. customis evaporated to dryness
  4. customthe resulting mixture is dried
  5. filtrationfiltered on celite
  6. customevaporated to dryness
  7. custom3.6 g of crude product (m.p. 170°-180° C.) are recovered
  8. customwhich product is chromatographed on silica (eluant: ethyl acetate/n-hexane, 2:1)
  9. customthe residue is then crystallized in ethanol

Sources & evidence

ORD record
ord-9b726cd346044399bc625eec8f760a75
Source dataset
uspto-grants-1991_08
Patent number
US05037822

Reaction notes

Loading…