Ammonium Chloride → HCID 68782421, compound

HRID 2097971Notes

Reaction equation

HRID 2097971 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)([O-])=O.[Cl-].[NH4+]>O.[Fe]>[N:9]1([C:5]2[S:6][CH:7]=[CH:8][C:4]=2[NH2:1])[CH:13]=[N:12][CH:11]=[N:10]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 68781704HCID 68781704, compound

Product 1

HCID 68782421HCID 68782421, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-nitrothiophen-2-yl)-1H-1,2,4-triazole (462 mg, 2.35 mmol), iron (1.31 g, 23.5 mmol) and ammonium chloride (163 mg, 3.06 mmol) in water (5 mL) was stirred at 100° C. for 18 h. The resulting suspension was filtered through a pad of diatomaceous earth and the filtrate was basified with aqueous NaOH. The aqueous solution was extracted with methylene chloride and the organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum to give 2-(1H-1,2,4-triazol-1-yl)thiophen-3-amine (314 mg, 1.89 mmol, 80%). Retention time (min)=0.454, method [1], MS (ESI) 167.0 (M+H).

Workup

  1. filtrationThe resulting suspension was filtered through a pad of diatomaceous earth
  2. extractionThe aqueous solution was extracted with methylene chloride
  3. customthe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5bc2082136394a73bebef9bdbba722a2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…