Stannous chloride dihydrate → HCID 12151696, compound

HRID 2406115Notes

Reaction equation

HRID 2406115 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-])=O)[N:5]=[CH:4][C:3]=1[C:16]([NH2:18])=[O:17].O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])[N:5]=[CH:4][C:3]=1[C:16]([NH2:18])=[O:17]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 121505645-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 12151696HCID 12151696, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.28 g (5.27 mmol) of 5-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carboxamide (Example 21A) are introduced into 30 ml of ethyl acetate and stirred with 5.8 g (25.8 mmol) of tin(II) chloride dihydrate at 70° C. for 16 hours. After cooling to room temperature, the solution is adjusted to pH 9-10 with saturated sodium bicarbonate solution. The tin salts precipitated thereby are filtered off through kieselguhr. The filtrate is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution. After drying over sodium sulphate, the solvent is removed in vacuo. 0.82 g (72% of theory) of the desired product is obtained.

Workup

  1. customThe tin salts precipitated
  2. filtrationthereby are filtered off through kieselguhr
  3. extractionThe filtrate is extracted with ethyl acetate
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialAfter drying over sodium sulphate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-af76e7e9399048458fdaef0c4dafce9b
Source dataset
uspto-grants-2014_08
Patent number
US08809348B2

Reaction notes

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