HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Hydroxide → N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)-2-nitro-N-phenylbenzenesulfonamide

HRID 404284
Notes
Print preview

Reaction equation

HRID 404284 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

HCID 58065830N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)-2-nitro-N-phenylbenzenesulfonamideYield 35.5%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
2×
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-519b848178a34234b70c1c2895b6026d
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748473B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes