Lawesson's reagent → 3-(4-Nitrophenyl)propanethioamide

HRID 30651Notes

Reaction equation

HRID 30651 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([NH2:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:24]2)=CC=1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[S:24])[NH2:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 135960733-(4-Nitrophenyl)propanamide

Product 1

HCID 826731463-(4-Nitrophenyl)propanethioamideYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(4-nitrophenyl)propanamide (0.50 g), 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (0.81 g) and pyridine (5 mL) was stirred at 50° C. for 15 hrs. The reaction mixture was concentrated, and 1N hydrochloric acid was added to the obtained residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 3-(4-nitrophenyl)propanethioamide as colorless crystals (0.40 g, yield 73%) from a fraction eluted with hexane-ethyl acetate (2:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 157-158° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22d7f84ecd6a4e7c9eb09f1b807031a5
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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