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

HRID 2247832Notes

Reaction equation

HRID 2247832 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>O1CCCC1>[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

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 103140701-[4-(1-Hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinone

Product 1

HCID 103597991-[4-(1-Hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinethione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 12.53 g of 1-[4-(1-hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinone, prepared as in Example 18 of the European Patent published under No. 0,033,578, and 7.5 g of Lawesson reagent (or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide) in 250 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). 7.3 g of product are recovered. M.p. 173°-175° C. After crystallization in a chloroform/n-hexane mixture, 6 g of expected pure product are obtained. M.p. 176°-178° 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. custom7.3 g of product are recovered
  6. customAfter crystallization in a chloroform/n-hexane mixture, 6 g of expected pure product
  7. customare obtained

Sources & evidence

ORD record
ord-caadda1b07134e45b64f0ace643836ac
Source dataset
uspto-grants-1991_08
Patent number
US05037822

Reaction notes

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