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

HRID 1378930Notes

Reaction equation

HRID 1378930 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]

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 6228DimethylformamideSolvent

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-0d1fb6ffc06e43188ce6fc596289c67e
Source dataset
uspto-grants-1997_09
Patent number
US05670452

Reaction notes

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