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

Participants

Role	Name	HCID	Charge
Reactant	Thiophenol	HCID 7969	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	N-[2-(3,9-dioxo-1,2,3,9,10,11-hexahydro-6H-dicyclopenta[c,g]carbazol-6-yl)ethyl]-2-nitrobenzenesulfonamide	HCID 71179221	—
Solvent	Methanol	HCID 887	—
Solvent	Chloroform	HCID 6212	—
Product	6-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione	HCID 45381116	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765738B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-60729c3cd6724113993915903b98b1af
Source note	uspto-grants-2014_07