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Citric Acid → 4-allyloxy-2-methyl-2H-indazole-3-sulfonamide

HRID 1734420
Notes
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Reaction equation

HRID 1734420 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[C:7]2[C:11]([CH:12]=[CH:13][CH:14]=1)=[N:10][N:9]([CH3:15])[C:8]=2[S:16]([NH2:19])(=[O:18])=[O:17].C(=O)([O-])O.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:1]([O:5][C:6]1[C:7]2[C:11]([CH:12]=[CH:13][CH:14]=1)=[N:10][N:9]([CH3:15])[C:8]=2[S:16]([NH2:19])(=[O:18])=[O:17])[CH:2]=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 135829371HCID 135829371, compound

Product 1

HCID 190831784-allyloxy-2-methyl-2H-indazole-3-sulfonamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

1.3 g of allyl bromide was added to a mixture comprising 5 g (22 mmol) of 4-hydroxy-2-methyl-2H-indazole-3-sulfonamide and 50 ml of a DMF solution of 1.9 g (22 mmol) of sodium hydrogencarbonate, and the mixture was stirred at room temperature for 12 hours. The mixture was poured into ice water, acidified with citric acid and extracted with ethyl acetate. The organic layer was washed, then concentrated and purified by column chromatography (hexane/ethyl acetate=2/1) to obtain 1.9 g (yield: 32.5%) of the desired product. Melting point: 143°-144° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. concentrationconcentrated
  4. custompurified by column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4616342051154c18b31c2f4e3a1ae372
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05534481

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes