Lawesson's reagent → 1-[3-(4-Cyano-phenyl)thiopropionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

HRID 379685Notes

Reaction equation

HRID 379685 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=O)=[CH:5][CH:4]=1)#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[S:42])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 111023311-[3-(4-Cyano-phenyl)propionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

Product 1

HCID 183668581-[3-(4-Cyano-phenyl)thiopropionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.9 g of 1-[3-(4-cyano-phenyl)propionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline are dissolved in 110 ml of toluene and boiled with 2.5 g Lawesson reagent [2,4-bis(4-methoxy-phenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide] for 1 hour at 110-120° C. Then the mixture is evaporated to dryness and the residue is chromatographed over a silica gel column with methylene chloride/ethyl acetate=19:1.

Workup

  1. customThen the mixture is evaporated to dryness
  2. customthe residue is chromatographed over a silica gel column with methylene chloride/ethyl acetate=19:1

Sources & evidence

ORD record
ord-e58bbc566cb1492fa65c574cd947779e
Source dataset
uspto-grants-2001_10
Patent number
US06300342B1

Reaction notes

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