Lawesson's reagent → Ethyl 4-[[3,5-bis(trimethylsilyl)benzenecarbothioyl]amino]cinnamate

HRID 2265111Notes

Reaction equation

HRID 2265111 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[CH:21]=[CH:20][C:12]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([C:6]([NH:8][C:9]2[CH:21]=[CH:20][C:12]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=2)=[S:40])[CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68487569Ethyl 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]cinnamate

Product 1

HCID 86644287Ethyl 4-[[3,5-bis(trimethylsilyl)benzenecarbothioyl]amino]cinnamateYield 149.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 17a (293 mg) was dissolved in toluene (8.34 ml), and Lawesson's reagent (189 mg) was added thereto in a nitrogen atmosphere. The obtained mixture was stirred while refluxing under heating for 2 hours. The solvent was distilled off, and the residue was purified by neutral silica gel column chromatography (10% ethyl acetate/n-hexane) to obtain Compound 17b (319 mg, 76%) as a yellow foam material.

Workup

  1. temperaturewhile refluxing
  2. temperatureunder heating for 2 hours
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by neutral silica gel column chromatography (10% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-9f10784424764065982f21584dd6c49c
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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