Hydrochloric Acid → HCID 70654331, compound

HRID 523038Notes

Reaction equation

HRID 523038 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:20]4[CH:21]=[CH:22][C:23]5[N:24](S(C6C=CC=CC=6)(=O)=O)[C:25]6[C:30]([C:31]=5[CH:32]=4)=[CH:29][C:28]([N:33]4[C:45]5[CH:44]=[CH:43][C:42]([C:46]7[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=7)=[CH:41][C:40]=5[C:39]5[C:34]4=[CH:35][CH:36]=[CH:37][CH:38]=5)=[CH:27][CH:26]=6)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl>CS(C)=O.O>[C:46]1([C:42]2[CH:43]=[CH:44][C:45]3[N:33]([C:28]4[CH:27]=[CH:26][C:25]5[NH:24][C:23]6[C:31]([C:30]=5[CH:29]=4)=[CH:32][C:20]([N:11]4[C:10]5[CH:9]=[CH:8][C:7]([C:1]7[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=7)=[CH:19][C:18]=5[C:17]5[C:12]4=[CH:13][CH:14]=[CH:15][CH:16]=5)=[CH:21][CH:22]=6)[C:34]4[C:39]([C:40]=3[CH:41]=2)=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 70654365HCID 70654365, compound

Product 1

HCID 70654331HCID 70654331, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

97 g (123 mmol) of 3,3″-bis(phenyl)-9′-[(phenyl)sulfonyl]-9,3′:6′,9″-ter-9H-carbazole and 48 g (856 mmol) of potassium hydroxide in 65 ml of dimethyl sulfoxide and 21 ml of water are heated under reflux for 1 h. The mixture is subsequently cooled to room temperature and neutralised using 1 M HCl solution. The mixture is then extracted with dichloromethane. The solvent is evaporated in vacuo, and the residue is purified by chromatography (heptane/ethyl acetate 10:1). Yield: 64.8 g (100 mmol), 80%.

Workup

  1. temperatureunder reflux for 1 h
  2. extractionThe mixture is then extracted with dichloromethane
  3. customThe solvent is evaporated in vacuo
  4. customthe residue is purified by chromatography (heptane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-7ec1e1daec74415eb752c37fb64bac92
Source dataset
uspto-grants-2016_05
Patent number
US09334260B2

Reaction notes

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