Lawesson's reagent → HCID 10314200, compound

HRID 2247829Notes

Reaction equation

HRID 2247829 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>O1CCCC1>[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, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 9.1 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 5.96 g of Lawesson reagent (or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide) in 180 cm3 of tetrahydrofuran is heated to reflux for 48 hours. The mixture is allowed to return to room temperature and is evaporated to dryness, and the residue is chromatographed on silica (eluant: benzene). 4.6 g of product are recovered. M.p. 195°-200° C. After crystallization in a chloroform/n-hexane mixture, 4.4 g of expected product are obtained. M.p. 209°-211° C.

Workup

  1. temperatureto reflux for 48 hours
  2. customto return to room temperature
  3. customis evaporated to dryness
  4. customthe residue is chromatographed on silica (eluant: benzene)
  5. custom4.6 g of product are recovered
  6. customAfter crystallization in a chloroform/n-hexane mixture, 4.4 g of expected product
  7. customare obtained

Sources & evidence

ORD record
ord-484f531726ae41f3ad6443d49d5d2a49
Source dataset
uspto-grants-1991_08
Patent number
US05037822

Reaction notes

Loading…