Ammonium Chloride → HCID 10712041, compound

HRID 654793Notes

Reaction equation

HRID 654793 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[N:14]=[C:13]([C:25]#[N:26])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][C:13]([C:25]#[N:26])=[N:14]2)=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10571030HCID 10571030, compound

Product 1

HCID 10712041HCID 10712041, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-[4-(methylsulfonyl)phenyl]-1-(4-nitrophenyl)pyrazole-3-carbonitrile (1.1 g), iron powder (1.1 g) and ammonium chloride (0.11 g) in ethanol (20 ml) and water (7 ml) was refluxed for 1 hour. The solvent was evaporated, and the residue was filtered, washed with water and dissolved in hot ethyl acetate. The solution was filtered and the filtrate was concentrated. The residue obtained was recrystallized from ethyl acetate to give crystals of 1-(4-aminophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carbonitrile (0.83 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customThe solvent was evaporated
  3. filtrationthe residue was filtered
  4. washwashed with water
  5. dissolutiondissolved in hot ethyl acetate
  6. filtrationThe solution was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue obtained
  9. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9b83d347eb9940c5aed22b9d916c054b
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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