Stannous Chloride → HCID 67267294, compound

HRID 598195Notes

Reaction equation

HRID 598195 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:9]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[N:8]=[C:7]([CH3:19])[C:6]=1[N+:20]([O-])=O)=[O:4].[Sn](Cl)Cl>C(=O)(O)[O-].[Na+]>[NH2:20][C:6]1[C:7]([CH3:19])=[N:8][N:9]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[C:5]=1[C:3]([NH:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 67266829HCID 67266829, compound

Product 1

HCID 67267294HCID 67267294, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N,3-dimethyl-4-nitro-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxamide (42 mg, 0.116 mmol) and tin (II) chloride (110 mg, 0.578 mmol) was stirred at 80° C. for 3 h and diluted with saturated sodium bicarbonate. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with 50% ethyl acetate/hexane to give the title compound (20 mg, 52%).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-5fa943aa08964bb18d08bb4b8fc597d4
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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