Lawesson's reagent → HCID 178501132, compound

HRID 1893339Notes

Reaction equation

HRID 1893339 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=O)[NH2:12])[CH2:7][CH2:6]1)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>O1CCCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=[S:23])[NH2:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178501131HCID 178501131, compound

Product 1

HCID 178501132HCID 178501132, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-4-carbamoyl-cyclohexanecarboxylic acid methyl ester (2.00 g, 10.8 mmol) and Lawesson's reagent (2.2 g, 5.4 mmol) in tetrahydrofuran (55 ml) was heated at reflux for 3.5 h. The heating bath was removed and the solvent was evaporated. The residue was purified by flash-chromatography with n-heptane/ethyl acetate as eluent to give a pink solid, which was triturated in toluene (10 ml). The precipitate was collected by filtration and dried in vacuo to give the title compound (1.04 g, 48%) as off-white solid. MS m/e: 202 ([M+H]+)

Workup

  1. temperatureat reflux for 3.5 h
  2. customThe heating bath was removed
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash-chromatography with n-heptane/ethyl acetate as eluent
  5. customto give a pink solid, which
  6. customwas triturated in toluene (10 ml)
  7. filtrationThe precipitate was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-aeaa2571c6364a1c99d547754e1a80d7
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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