Nitrogen → HCID 67127834, compound

HRID 2040047Notes

Reaction equation

HRID 2040047 reaction equation
N#N.[F:3][C:4]([C:7]1[O:11][C:10]([CH2:12][N:13]2[N:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[N:14]2)=[CH:9][CH:8]=1)([F:6])[CH3:5].[NH4+].[Cl-]>CCO.O.[Fe]>[F:6][C:4]([C:7]1[O:11][C:10]([CH2:12][N:13]2[N:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)=[CH:9][CH:8]=1)([F:3])[CH3:5]

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 67127936HCID 67127936, compound

Product 1

HCID 67127834HCID 67127834, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-[5-(1,1-difluoro-ethyl)-furan-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole (471 mg, 1.82 mmol), iron powder (309 mg, 5.47 mmol) and NH4Cl (493 mg, 9.12 mmol) in a mixture of EtOH (7.0 mL) and water (3.5 mL) was stirred at 85° C. for 20 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 MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=0.82 min; [M+H+AcCN]+=270.24.

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 MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-1ffe5f5e4e264aaaaba708f7dce6bf0d
Source dataset
uspto-grants-2013_11
Patent number
US08580831B2

Reaction notes

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