Lawesson's reagent → 6,11-Dihydro-N-(2,6-diisopropylphenyl)-2-methyldibenz[b,e]oxepin-11-carbothioamide

HRID 2260590Notes

Reaction equation

HRID 2260590 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([CH:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][O:19][C:18]2[CH:27]=[CH:28][C:29]([CH3:31])=[CH:30][C:17]1=2)=O)([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([CH:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][O:19][C:18]2[CH:27]=[CH:28][C:29]([CH3:31])=[CH:30][C:17]1=2)=[S:41])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3072807Dibenz(b,e)oxepin-11-carboxamide, 6,11-dihydro-N-(2,6-bis(1-methylethyl)phenyl)-2-methyl-

Product 1

HCID 104553336,11-Dihydro-N-(2,6-diisopropylphenyl)-2-methyldibenz[b,e]oxepin-11-carbothioamideYield 96.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After 1.09 g of Compound 4 obtained in Example 4 was dissolved in 10 ml of toluene, 1.07 g of Lawesson's reagent was added to the solution. The mixture was heated under reflux for an hour. The reaction mixture was allowed to stand at room temperature, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (2:1)] to obtain 1.46 g of a crude product. The crude product was recrystallized from ethyl acetate-hexane to obtain 1.09 g of Compound 36.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for an hour
  3. customto stand at room temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (2:1)]
  6. customto obtain 1.46 g of a crude product
  7. customThe crude product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ab9b161e45c343ca9daa8c8693bf846c
Source dataset
uspto-grants-1995_12
Patent number
US05478835

Reaction notes

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