Formic Acid → HCID 178506083, compound

HRID 1523328Notes

Reaction equation

HRID 1523328 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](=S)[NH2:7].O.[NH2:19][NH2:20].[CH:21](O)=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:6]2[N:7]=[CH:21][NH:20][N:19]=2)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 28069243,5-DI(Trifluoromethyl)benzene-1-carbothioamide

Product 1

HCID 178506083HCID 178506083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 5-L, 3-necked, round-bottomed flask was charged with a solution of 3,5-bis(trifluoromethyl)benzothioamide (205.65 g) in DMF (1.03 L). Hydrazine hydrate (73.2 mL, 2.0 eq.) was added dropwise and the reaction mixture was stirred at RT for 1 h. HCOOH (1.03 L) was added dropwise and the reaction mixture was refluxed at 90° C. for 3 hours. After being allowed to cool to RT, the reaction mixture was poured into saturated aqueous sodium bicarbonate solution (7 L) and extracted with EtOAc (3×1 L). The combined organic layers were washed with aqueous saturated brine (3×500 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure (35° C., 20 mmHg) to afford 180 g of crude compound. This crude material was stirred with petroleum ether (3×500 mL), filtered and dried to obtain 160 g. of 3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole obtained as a pale yellow solid (yield: 75%).

Workup

  1. temperaturethe reaction mixture was refluxed at 90° C. for 3 hours
  2. temperatureto cool to RT
  3. extractionextracted with EtOAc (3×1 L)
  4. washThe combined organic layers were washed with aqueous saturated brine (3×500 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (35° C., 20 mmHg)
  8. customto afford 180 g of crude compound
  9. filtrationfiltered
  10. customdried
  11. customto obtain 160 g

Sources & evidence

ORD record
ord-aa77d34cb95944e289595a0966183cf6
Source dataset
uspto-grants-2015_07
Patent number
US09079865B2

Reaction notes

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