Hydrochloric Acid → HCID 67464347, compound

HRID 2281176Notes

Reaction equation

HRID 2281176 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12](S(C4C=CC=CC=4)(=O)=O)[C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl>CS(C)=O.O>[C:1]1([C:7]2[O:8][CH:9]=[C:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[NH:12][C:11]=23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 104070034H-Furo[3,4-b]indole, 3-phenyl-4-(phenylsulfonyl)-

Product 1

HCID 67464347HCID 67464347, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

45 g (123 mmol) of 3-phenyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole and 48 g (856 mmol) of potassium hydroxide in 65 ml of DMSO and 21 ml of water are heated under reflux for 1 h. The mixture is subsequently cooled to room temperature, neutralised using 1M 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: 22.4 g (96 mmol), 80%.

Workup

  1. temperatureunder reflux for 1 h
  2. extractionextracted 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-a0631ac15b5a422ba9876dcaa1b17a25
Source dataset
uspto-grants-2015_09
Patent number
US09139582B2

Reaction notes

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