Acetic Acid → HCID 178507667, compound

HRID 402341Notes

Reaction equation

HRID 402341 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[C:9]([SH:18])=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)([O-])=O.C(OCC)(=O)C>[Fe].O>[NH2:5][C:8]1[C:9]([SH:18])=[N:10][CH:11]=[C:12]([C:14]([F:16])([F:15])[F:17])[CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 178526654HCID 178526654, compound

Product 1

HCID 178507667HCID 178507667, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 2.87 g of iron, 10 ml of acetic acid and 10 ml of water was added a mixture of 3.84 g of 3-nitro-5-(trifluoromethyl)pyridine-2-thiol and 10 ml of ethyl acetate at 70° C. over a period of 10 minutes. The reaction mixture was cooled down to room temperature, then, to the reaction mixture was added water, and the resultant mixture was extracted with ethyl acetate twice. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure to obtain 3.1 g of 3-amino-5-(trifluoromethyl)pyridine-2-thiol.

Workup

  1. additionwas added
  2. extractionthe resultant mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af22bcece51d41c3a2a4f8ba67c5f015
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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