Potassium Hydroxide → HCID 58065830, compound

HRID 332091Notes

Reaction equation

HRID 332091 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:13])([O-:5])=[O:4].[Br:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH2:37][CH2:38][CH2:39]Br)[C:28]3[C:33]([C:34]=2[CH:35]=1)=[CH:32][C:31]([Br:36])=[CH:30][CH:29]=3>CN(C=O)C.CCOC(C)=O>[Br:36][C:31]1[CH:30]=[CH:29][C:28]2[N:27]([CH2:37][CH2:38][CH2:39][N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[S:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N+:3]([O-:5])=[O:4])(=[O:14])=[O:13])[C:26]3[C:34]([C:33]=2[CH:32]=1)=[CH:35][C:23]([Br:22])=[CH:24][CH:25]=3

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 2296002-Nitro-N-phenylbenzenesulfonamideHCID 580972043,6-dibromo-9-(3-bromopropyl)-9H-carbazole

Product 1

HCID 58065830HCID 58065830, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Crushed KOH (0.0024 g, 0.0431 mmol) was added to 2-nitro-N-phenylbenzenesulfonamide (0.0100 g, 0.0359 mmol) in 0.2 mL DMF solution and the mixture was stirred for 30 min. 3,6-dibromo-9-(3-bromopropyl)-9H-carbazole (Example 35, 0.0240 g, 0.0538 mmol) in 0.3 mL DMF solution was added dropwise into the mixture and it was stirred at room temperature overnight. The crude reaction mixture was diluted with 20 mL EtOAc and washed with water 5×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.0082 g white solid as impure product, purity 66.9% (impurity is starting Ns-aniline; used without additional purification), yield 35.5%.

Workup

  1. stirringwas stirred at room temperature overnight
  2. customThe crude reaction mixture
  3. washwashed with water 5×10 mL
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customevaporated
  6. customto afford the crude product, which

Sources & evidence

ORD record
ord-b27ca8733ec74555a1cf56a1a9ab0d66
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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