Lawesson's reagent → 4-(2,3-Dichlorophenyl)pyrrole-3-thiocarboxamide

HRID 1975398Notes

Reaction equation

HRID 1975398 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:14]([NH2:16])=O)=[CH:11][NH:12][CH:13]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1.CCCCCC.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:14](=[S:26])[NH2:16])=[CH:11][NH:12][CH:13]=1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 200936224-(2,3-Dichlorophenyl)-1H-pyrrole-3-carboxamideHCID 21226206Ethyl acetate hexane

Product 1

HCID 200936264-(2,3-Dichlorophenyl)pyrrole-3-thiocarboxamideYield 104.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2,3-dichlorophenyl)pyrrole-3-carboxamide (0.98 g, 3.8 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (0.77 g, 1.9 mmol) in tetrahydrofuran is heated at reflux for 75 minutes, cooled and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and a 1:1 hexane/ethyl acetate mixture gives the title product as a yellow solid (0.54 g, mp 128°-132° C.).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 75 minutes
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-4e62572999ea4bcca171fdad8cf1b035
Source dataset
uspto-grants-1994_02
Patent number
US05286742

Reaction notes

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