Lawesson's reagent → 4-Thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate

HRID 18634Notes

Reaction equation

HRID 18634 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:24])[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=O)[NH2:22])=[CH:17][CH:16]=2)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].COC1C=CC2C(=CC=C(C(C)C(OC3C=CC(C4[S:48]SC(=S)C=4)=CC=3)=O)C=2)C=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>C1C=CC=CC=1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:24])[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[S:48])[NH2:22])=[CH:17][CH:16]=2)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 250659864-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoateHCID 593455894-Carbamoylphenyl 2-(4-isobutylphenyl)propanoate

Product 1

HCID 250657684-Thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoateYield 55%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate, 3 (2.48 g, 7.62 mmol) and Lawesson reagent (3.1 g, 7.62 mmol) were dissolved in 130 ml of anhydrous benzene. The reaction was warmed to 60° C. and stirred for 4 h. The solvent was removed under reduced pressure. The obtained compound was purified by a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5) giving the pure compound 4 (1.45 g, 55% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe obtained compound was purified by a silica gel open column
  3. washeluted with CH2Cl2/MeOH (9.5/0.5)

Sources & evidence

ORD record
ord-5f52b93a31fb4e17a8175ed2b25290f5
Source dataset
uspto-grants-2010_06
Patent number
US07741359B2

Reaction notes

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