Thiophenol → N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)aniline

HRID 1811486Notes

Reaction equation

HRID 1811486 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH2:17][CH2:18][N:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH2:17][CH2:18][NH:19][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 58065830HCID 58065830, compound

Product 1

HCID 46851212N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)anilineYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)-2-nitro-N-phenylbenzenesulfonamide (0.0378 g, 0.0588 mmol, 1 equiv), cesium carbonate (0.0574 g, 0.176 mmol, 3 equiv) and benzenethiol (0.0194 g, 0.176 mmol) were mixed in 1 mL anhydrous THF. The mixture was stirred at room temperature for 3 hours. THF was removed under vacuum and the residue was purified by silica gel chromatography using Hexanes/EtOAc to afford 0.0164 g colorless oil as product, yield 60.9%.

Workup

  1. customTHF was removed under vacuum
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4acb5ab8aa1a4def91307e18049a5d37
Source dataset
uspto-grants-2013_01
Patent number
US08362277B2

Reaction notes

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