Water → 1-(3,4-Dichlorobenzyl)-2-(2-hydroxy-5-nitrobenzyl)-5-methylthio-1,2-dihydroindazol-3-one hydrate

HRID 567725

Reaction equation

HRID 567725 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15][CH3:16])=[CH:12][CH:13]=2)[C:8]([OH:17])=[N:7]1.[H-].[Na+].[OH:24][C:25]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:26]=1[CH2:27]Cl.O>CS(C)=O>[OH2:17].[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15][CH3:16])=[CH:12][CH:13]=2)[C:8](=[O:17])[N:7]1[CH2:27][C:26]1[CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=[CH:32][C:25]=1[OH:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 763052-(Chloromethyl)-4-nitrophenolHCID 178503082HCID 178503082, compound

Product 1

HCID 212627051-(3,4-Dichlorobenzyl)-2-(2-hydroxy-5-nitrobenzyl)-5-methylthio-1,2-dihydroindazol-3-one hydrate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

3.6 g (11 mmol) of 1-(3,4-dichlorobenzyl)-5-methylthio-1H-indazol-3-ol are dissolved in 100 ml of DMSO and treated in portions with 0.34 g (13.2 mmol) of sodium hydride (95 percent). After stirring for 2 hours, a solution of 2.1 g (11 mmol) of 2-hydroxy-5-nitrobenzyl chloride in 20 ml of DMSO is added dropwise and the mixture is stirred at 60° C. for 3 hours. After cooling, 200 ml of water are added dropwise, the mixture is stirred for 4 hours and the solid is filtered off with suction. The precipitate is extracted by stirring with methanol whilst hot and recrystallized from 2-propanol.

Workup

  1. stirringthe mixture is stirred at 60° C. for 3 hours
  2. temperatureAfter cooling
  3. stirringthe mixture is stirred for 4 hours
  4. filtrationthe solid is filtered off with suction
  5. extractionThe precipitate is extracted
  6. stirringby stirring with methanol whilst hot and
  7. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-0dc3658d526748e18bebe64c0ad5583e
Source dataset
uspto-grants-2001_01
Patent number
US06180637B2

Linked notes

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