Ethanol → HCID 22661019, compound

HRID 392780Notes

Reaction equation

HRID 392780 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[N:13][C:12]([C:25]([F:28])([F:27])[F:26])=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:19][CH:20]=3)=[N:13][C:12]([C:25]([F:26])([F:27])[F:28])=[N:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 22661022HCID 22661022, compound

Product 1

HCID 22661019HCID 22661019, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-(4-nitro-phenyl)-5-(4-methylsulfonyl-phenyl)-3-trifluoromethyl-1H-1,2,4-triazole (1.2 g, 2.91 mmol), iron powder (0.8 g, 14.27 mmol), ammonium chloride (0.80 g, 1.45 mmol), ethanol (25 ml) and water (13 ml) was heated to reflux for 1 hour, then cooled and filtered. The filtrate was poured onto water, extracted with ethyl acetate and a dichloromethane/methanol solution. The organic extracts were washed with saturated brine, dried over Na2SO4 and evaporated to give a yellow powder (1 g, 91%), which was used for the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. additionThe filtrate was poured onto water
  6. extractionextracted with ethyl acetate
  7. washThe organic extracts were washed with saturated brine
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-64368b3adb024d1daff064e372443bb1
Source dataset
uspto-grants-2004_10
Patent number
US06803380B1

Reaction notes

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