Ammonium Chloride → HCID 22439210, compound

HRID 963106Notes

Reaction equation

HRID 963106 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:39]=[CH:38][CH:37]=[CH:36][C:5]=1[C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=1[N:15]1[C:19]([CH3:20])=[N:18][N:17]=[C:16]1[CH2:21][NH:22][C:23](=[O:35])/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-])=O)=[O:7]>C(O)C.O.[Fe]>[Cl:3][C:4]1[CH:39]=[CH:38][CH:37]=[CH:36][C:5]=1[C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=1[N:15]1[C:19]([CH3:20])=[N:18][N:17]=[C:16]1[CH2:21][NH:22][C:23](=[O:35])/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32])=[O:7]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22439207HCID 22439207, compound

Product 1

HCID 22439210HCID 22439210, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ammonium chloride (118 mg) and iron powder (1.0 g) were dissolved in a mixed solvent of ethanol (15 ml) and water (5 ml). trans-N-(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-(2-nitrophenyl)propenamide (1.07 g) was carefully added under reflux to the reaction mixture, and the mixture was refluxed for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was concentrated under reduced pressure. The obtained solid was recrystallized from ethyl acetate to give 0.60 g of trans-N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-(2-aminophenyl)propenamide.

Workup

  1. temperatureunder reflux to the reaction mixture
  2. temperaturethe mixture was refluxed for 1 hour
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure
  9. customThe obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2c0cdeaebdc344c5b29979cd0f729186
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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