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

HRID 1742650

Reaction equation

HRID 1742650 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
  6. customhexane-ethyl acetate (2:1 )]to obtain 1.46 g of a crude product
  7. customThe crude product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d8e661bcd65c49a49de6dd8233e94387
Source dataset
uspto-grants-1994_08
Patent number
US05340807

Linked notes

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