Lawesson's reagent → HCID 86755857, compound

HRID 1954760Notes

Reaction equation

HRID 1954760 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Cl:23][C:24]1[CH:44]=[CH:43][C:27]2[C:28](=[O:42])[C:29]3[C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[N:35][NH:34][C:30]=3[C:31](=O)[NH:32][C:26]=2[CH:25]=1>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:44]=[CH:43][C:27]2[C:28](=[O:42])[C:29]3[C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[N:35][NH:34][C:30]=3[C:31](=[S:10])[NH:32][C:26]=2[CH:25]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 1784704817-Chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10-(1H,9H)dione

Product 1

HCID 86755857HCID 86755857, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of Lawesson's Reagent [(2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide)(0.32 g, 0.80 mmol) in dry toluene (15 mL) at room temperature was added 7-chloro-3-(ethoxycarbonyl)pyrazolo-[3,4-c][1]benzazepine-4,10(1H,9H )-dione (0.51 g, 1.59 mmol) in one portion. The resulting slurry was heated to reflux for 1.5 hours. The reaction mixture was filtered to remove insoluble material. The filtrate was concentrated via rotary evaporator to give a green oil which was purified by flash chromatography using chloroform:methanol (9:1) as the eluent. The yellow-green solid recovered was recrystallized from methanol to give the title compound (0.44 g, 82%, mp 248.0-252.6° C.).

Workup

  1. temperatureThe resulting slurry was heated
  2. temperatureto reflux for 1.5 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove insoluble material
  5. concentrationThe filtrate was concentrated via rotary evaporator
  6. customto give a green oil which
  7. customwas purified by flash chromatography
  8. customThe yellow-green solid recovered
  9. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-fca3fe79007b470298473d017472d5d8
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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