Lawesson's reagent → 1-[4-(1-Hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinethione

HRID 2247831Notes

Reaction equation

HRID 2247831 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=O)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.COC1C=CC(P2SP(C3C=CC(OC)=CC=3)S2)=CC=1>C(COC)OC>[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[S:32])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 103140701-[4-(1-Hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinoneHCID 127328752,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane

Product 1

HCID 103597991-[4-(1-Hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinethioneYield 57.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture comprising 5 g of 1-[4-(1-hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinone, prepared as in Example 18 of the European Patent Application published under No. 0,033,578, and 3.13 g of Lawesson reagent (or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane in 100 cm3 of dimethoxyethane is heated to reflux for 3 hours. The mixture is allowed to return to room temperature and is evaporated to dryness, and the residue is chromatographed on silica (eluant: benzene). 2 g of product are recovered. M.p. 168°-170° C. After crystallization in methanol, 1.5 g of expected product are obtained. M.p. 172°-173° C.

Workup

  1. temperatureto reflux for 3 hours
  2. customto return to room temperature
  3. customis evaporated to dryness
  4. customthe residue is chromatographed on silica (eluant: benzene)
  5. custom2 g of product are recovered
  6. customAfter crystallization in methanol

Sources & evidence

ORD record
ord-6e3a5dd5f765421fb65cc03a736ba03d
Source dataset
uspto-grants-1991_08
Patent number
US05037822

Reaction notes

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