Lawesson's reagent → HCID 10181892, compound

HRID 2265374Notes

Reaction equation

HRID 2265374 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=O)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[S:42])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9845390HCID 9845390, compound

Product 1

HCID 10181892HCID 10181892, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.79 g) in toluene (10 mL) was added Lawesson's reagent (0.9 g), and the mixture was heated under reflux for 5 hr. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carbothioamide (0.19 g). melting point: 123-125° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dbaa148687674e7fa6fcbd308fe4bf16
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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