Hydrochloric Acid → HCID 178507235, compound

HRID 1586361Notes

Reaction equation

HRID 1586361 reaction equation
[Cl:1][C:2]1[C:3]([C:7]2[C:15]3[O:14][C:13]([F:17])([F:16])[O:12][C:11]=3[CH:10]=[CH:9][C:8]=2[N+:18]([O-])=O)=[N:4][NH:5][CH:6]=1.Cl.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([C:7]2[C:15]3[O:14][C:13]([F:16])([F:17])[O:12][C:11]=3[CH:10]=[CH:9][C:8]=2[NH2:18])=[N:4][NH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 178526434HCID 178526434, compound

Product 1

HCID 178507235HCID 178507235, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

6.0 g (0.02 mol) of 4-chloro-3-(2,2-difluoro-5-nitrobenzo-1,3-dioxol-4-yl)pyrazole, in solution in 60 ml of ethanol, are run, at room temperature, onto a mixture of 30 ml of 36% HCl and 20.2 g (0.09 mol) of SnCl2 2H2O in 60 ml of ethanol. The reaction mixture is stirred for 2 h at room temperature, neutralised with 10% NaOH and then filtered. The insoluble material is washed with ethanol. The alcohol phase is concentrated under reduced pressure and the residue is taken up in ethyl acetate. After drying the organic phase and concentration under vacuum, the residue is triturated with 50 ml of heptane, filtered and dried. We obtain 4.6 g of 4-chloro,3-(5-amino,2,2-difluorobenzo-1,3-dioxol-4-yl)pyrazole melting at 195° C. (yield 84%).

Workup

  1. filtrationfiltered
  2. washThe insoluble material is washed with ethanol
  3. concentrationThe alcohol phase is concentrated under reduced pressure
  4. customAfter drying
  5. concentrationthe organic phase and concentration under vacuum
  6. customthe residue is triturated with 50 ml of heptane
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-7c4e3fed6255492ab1fea84da9bcf974
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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