Lawesson's reagent → HCID 10314200, compound

HRID 2247828Notes

Reaction equation

HRID 2247828 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=O)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C(COC)OC>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[S:31])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 10425405HCID 10425405, compound

Product 1

HCID 10314200HCID 10314200, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture comprising 5 g of 1-[4-(1-piperidyl)benzenesulphonyl]-2-pyrrolidinone, prepared as in Example 10 of the European Patent published under No. 0,033,578, and 3.28 g of Lawesson reagent (or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide) in 100 cm3 of dimethoxyethane is heated to reflux for 1 hour. The mixture is allowed to return to room temperature and is evaporated to dryness, and the residue is chromatographed on silica (eluant: ethyl acetate/n-hexane, 1:1). 3.5 g of product are recovered. M.p. 195°-200° C. After crystallization in ethanol, 1.5 g of expected product are obtained. M.p. 211°-212° C.

Workup

  1. temperatureto reflux for 1 hour
  2. customto return to room temperature
  3. customis evaporated to dryness
  4. customthe residue is chromatographed on silica (eluant: ethyl acetate/n-hexane, 1:1)
  5. custom3.5 g of product are recovered
  6. customAfter crystallization in ethanol

Sources & evidence

ORD record
ord-04f4664a29c9442abb89382a6d86e2f8
Source dataset
uspto-grants-1991_08
Patent number
US05037822

Reaction notes

Loading…