Thiophenol → 6-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

HRID 514777Notes

Reaction equation

HRID 514777 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH2:22][CH2:23][NH:24]S(C4C=CC=CC=4[N+]([O-])=O)(=O)=O)[C:11]4[CH:12]=[CH:13][C:14]5[C:20](=[O:21])[CH2:19][CH2:18][C:15]=5[C:16]=4[C:17]=3[C:5]=2[CH2:4][CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[NH2:24][CH2:23][CH2:22][N:10]1[C:11]2[CH:12]=[CH:13][C:14]3[C:20](=[O:21])[CH2:19][CH2:18][C:15]=3[C:16]=2[C:17]2[C:5]3[CH2:4][CH2:3][C:2](=[O:1])[C:6]=3[CH:7]=[CH:8][C:9]1=2

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 71179221N-[2-(3,9-dioxo-1,2,3,9,10,11-hexahydro-6H-dicyclopenta[c,g]carbazol-6-yl)ethyl]-2-nitrobenzenesulfonamide

Product 1

HCID 453811166-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Compound 58 (2.2 g, 4.38 mmol) was suspended in a mixture of chloroform (200 mL) and methanol (200 mL). Then Cs2CO3 (4.3 g, 13.20 mmol) and at once PhSH (1.3 mL, 12.74 mmol) were added. The solution was refluxed for 18 h (LC/MS monitoring) and evaporated to dryness. Then, an aqueous solution of citric acid was added. The solution obtained was neutralized with an aqueous NaHCO3 solution. The precipitate was filtered off, washed with CH3CN and ether. The product isolated was used in the next step without purification.

Workup

  1. temperatureThe solution was refluxed for 18 h (LC/MS monitoring)
  2. customevaporated to dryness
  3. additionThen, an aqueous solution of citric acid was added
  4. customThe solution obtained
  5. filtrationThe precipitate was filtered off
  6. washwashed with CH3CN and ether
  7. customThe product isolated
  8. customwas used in the next step without purification

Sources & evidence

ORD record
ord-63f3e494fa154716bd576831fca8dd60
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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