Nitrogen → HCID 67958086, compound

HRID 82840Notes

Reaction equation

HRID 82840 reaction equation
N#N.[CH3:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[N:13]2)[O:9][CH:10]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([NH2:17])[CH:14]=[N:13]2)[O:9][CH:10]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 67958050HCID 67958050, compound

Product 1

HCID 67958086HCID 67958086, 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 4-(methoxymethyl)-2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazole (1.46 g, 6.10 mmol), iron powder (1.03 g, 18.31 mmol) and NH4Cl (1.65 g, 30.52 mmol) in a mixture of EtOH (30.0 mL) and water (15.0 mL) was stirred at 85° C. for 15 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (55 mL) was added followed by 1N NaOH (33 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (5×50 mL). 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 07: tR=0.42 min; [M+H]+=210.09.

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 (55 mL) was added
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with CH2Cl2 (5×50 mL)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-df94260533a64b819a189a72fd83f85b
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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