Ammonium Chloride → HCID 23498803, compound

HRID 1836113Notes

Reaction equation

HRID 1836113 reaction equation
[CH:1]1([C:6]2[C:10]([N+:11]([O-])=O)=[C:9]([C:14]([NH2:16])=[O:15])[O:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>O.[Zn]>[NH2:11][C:10]1[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:7][O:8][C:9]=1[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 23498800HCID 23498800, compound

Product 1

HCID 23498803HCID 23498803, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3.15 g (13.9 mmol) of 3-cyclopentyl-4-nitro-isoxazole-5-carboxamide (example V) and 17.51 g (327 mmol) of ammonium chloride are suspended in 70 ml of water and the suspension is cooled to 0° C. 8.5 g (118 mmol) of zinc powder are added in small portions while stirring vigorously. The reaction mixture is stirred at room temperature for 30 minutes. For the working up, filtration takes place through kieselguhr with the kieselguhr subsequently being washed with ethyl acetate, and the filtrate is evaporated to dryness in vacuo. The residue is triturated with ethyl acetate. After filtering, the solvent is removed in vacuo. 1.95 g (70%) of colorless solid are obtained.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 30 minutes
  2. filtrationFor the working up, filtration
  3. washsubsequently being washed with ethyl acetate
  4. customthe filtrate is evaporated to dryness in vacuo
  5. customThe residue is triturated with ethyl acetate
  6. filtrationAfter filtering
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-f56af3ada49c4afe9e521916ea36a705
Source dataset
uspto-grants-2004_08
Patent number
US06777416B2

Reaction notes

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