Nitrogen → HCID 66928580, compound

HRID 2065018Notes

Reaction equation

HRID 2065018 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][CH:12]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[S:13][CH:12]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 66929242HCID 66929242, compound

Product 1

HCID 66928580HCID 66928580, 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 mixture of 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-3-ylmethyl]-4-nitro-1H-pyrazole (220 mg, 0.75 mmol), iron powder (126 mg, 2.24 mmol) and NH4Cl (201 mg, 3.73 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (25 mL) was added followed by 1M NaOH (25 mL). The aq. layer was extracted with CH2Cl2 (2×25 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a red oil. LC-MS-conditions 02: tR=0.63 min; [M+H]+=266.09.

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 (25 mL) was added
  4. extractionThe aq. layer was extracted with CH2Cl2 (2×25 mL)
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-6e80a2993314420399818fec31f48b5b
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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