Nitrogen → HCID 66929097, compound

HRID 2065076Notes

Reaction equation

HRID 2065076 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[O:13][CH:14]=[C:15]([C:17](=[O:19])[CH3:18])[N:16]=2)[N:7]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:3][C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[O:13][CH:14]=[C:15]([C:17](=[O:19])[CH3:18])[N:16]=2)[N:7]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 669287371-[2-(3-Nitro-pyrazol-1-ylmethyl)-oxazol-4-yl]-ethanone

Product 1

HCID 66929097HCID 66929097, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[2-(3-nitro-pyrazol-1-ylmethyl)-oxazol-4-yl]-ethanone (48 mg, 0.20 mmol), iron powder (34 mg, 0.61 mmol) and NH4Cl (56 mg, 1.03 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 60 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (10 mL) was added followed by water (10 mL). The aq. layer was extracted with CH2Cl2 (2×10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC: rf (EA)=0.13. LC-MS-conditions 02: tR=0.38 min; [M+H]+=207.40.

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 (10 mL) was added
  4. extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-065d5d1b02a6444788ac01409187c053
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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