Hydrochloric Acid → methyl 9H-[1,9']bicarbazolyl-1'-carboxylate

HRID 531896Notes

Reaction equation

HRID 531896 reaction equation
C1(S([N:10]2[C:22]3[C:21]([N:23]4[C:35]5[C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:33][CH:32]=[CH:31][C:30]=5[C:29]5[C:24]4=[CH:25][CH:26]=[CH:27][CH:28]=5)=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=O)=O)C=CC=CC=1.[OH-].[K+].Cl>CS(C)=O.O>[C:21]1([N:23]2[C:35]3[C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:33][CH:32]=[CH:31][C:30]=3[C:29]3[C:24]2=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:22]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68243195methyl 9-benzenesulfonyl-9H-[1,9']bicarbazolyl-1'-carboxylate

Product 1

HCID 67404015methyl 9H-[1,9']bicarbazolyl-1'-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

65 g (123 mmol) of methyl 9-benzenesulfonyl-9H-[1,9′]bicarbazolyl-1′-carboxylate and 48 g (856 mmol) of potassium hydroxide in 65 ml of dimethyl sulfoxide and 21 ml of water are heated at 60° C. for 1 h. The mixture is subsequently cooled to room temperature, neutralised using 1 M HCl solution and extracted with dichloromethane. The solvent is evaporated in vacuo, and the residue is purified by chromatography (heptane/ethyl acetate 10:1). Yield: 45 g (116 mmol), 95% of theory.

Workup

  1. extractionextracted with dichloromethane
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is purified by chromatography (heptane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-f5cd4b4082a54345a2eb34f74d75083d
Source dataset
uspto-grants-2016_05
Patent number
US09356243B2

Reaction notes

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