Lawesson's reagent → HCID 86672762, compound

HRID 1754956Notes

Reaction equation

HRID 1754956 reaction equation
[CH:1]1([C:7]2[NH:11][C:10](=O)[C:9]3([CH2:17][CH2:16][N:15]([S:18]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[NH:11][C:10](=[S:39])[C:9]3([CH2:17][CH2:16][N:15]([S:18]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66815925HCID 66815925, compound

Product 1

HCID 86672762HCID 86672762, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2-Cyclohexyl-8-(2-o-tolyl-ethanesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (24.2 mg, 0.058 mmol), Lawesson's reagent (48.3 mg, 0.116 mmol) and toluene (1.16 ml) were added to a sealed test tube and stirred at 110° C. overnight. The reaction mixture was cooled to ambient temperature, and the solvent was then distilled off under reduced pressure. The residue was purified by column chromatography (silica gel, CH2Cl2-MeOH) to give 2-cyclohexyl-8-(2-o-tolyl-ethanesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-4-thione (11.2 mg, 45%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. distillationthe solvent was then distilled off under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel, CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-eba33d984b4745fc859bcd791cb0ff08
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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