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

4-Toluenesulfonyl chloride → 6,6-diphenyl-1-(4-toluenesulphonyl)-6,7-dihydro-1H-indazol-3-carboxylic acid

HRID 1243836
Notes
Print preview

Reaction equation

HRID 1243836 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]1([C:18]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][C:25]3[NH:24][N:23]=[C:22]([C:27]([OH:29])=[O:28])[C:21]=3[CH:20]=[CH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)C.O.[OH-].[Na+]>[C:30]1([C:18]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:26][C:25]3[N:24]([S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=4)(=[O:9])=[O:8])[N:23]=[C:22]([C:27]([OH:29])=[O:28])[C:21]=3[CH:20]=[CH:19]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 219286736,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxylic acid

Product 1

HCID 219291026,6-diphenyl-1-(4-toluenesulphonyl)-6,7-dihydro-1H-indazol-3-carboxylic acidYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283
Diethyl Ether
Solvent
HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1 g of p-toluenesulphonyl chloride in 10 cm3 of diethyl ether is added, at a temperature in the region of 20° C., to a solution of 1 g of 6,6-diphenyl-6,7-dihydro-1H-indazol-3-carboxylic acid in 10 cm3 of water and 10 cm3 of a normal aqueous sodium hydroxide solution. The reaction mixture, which sets to a solid after about ten minutes of vigorous stirring, is diluted with 10 cm3 of water. After stirring for about eighteen hours at a temperature in the region of 20° C., the reaction mixture is filtered. The solid is washed with three times 20 cm3 of water and then suspended in 20 cm3 of water. 10 cm3 of a normal aqueous hydrochloric acid solution are added. The mixture is extracted with three times 50 cm3 of ethyl acetate. The combined organic phases are successively washed with three times 70 cm3 of water and once 70 cm3 of saturated aqueous sodium chloride solution and then dried over magnesium sulphate, filtered and concentrated under reduced pressure (13 kPa). The residue is purified by flash chromatography on a column of silica [eluent: dichloromethane/methanol (95/5 by volume)]. 0.94 g of 6,6-diphenyl-1-(4-toluenesulphonyl)-6,7-dihydro-1H-indazol-3-carboxylic acid is thus obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. waitThe reaction mixture, which sets to a solid after about ten minutes of vigorous stirring
  2. filtrationthe reaction mixture is filtered
  3. washThe solid is washed with three times 20 cm3 of water
  4. addition10 cm3 of a normal aqueous hydrochloric acid solution are added
  5. extractionThe mixture is extracted with three times 50 cm3 of ethyl acetate
  6. washThe combined organic phases are successively washed with three times 70 cm3 of water and once 70 cm3 of saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (13 kPa)
  10. customThe residue is purified by flash chromatography on a column of silica [eluent: dichloromethane/methanol (95/5 by volume)]

Sources & evidence

ORD record
ord-bf7deb67199b468cb630d1e5704be87f
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07119115B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes