Nitrogen → HCID 67958713, compound

HRID 527244Notes

Reaction equation

HRID 527244 reaction equation
N#N.[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[N:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[N:20]3)[O:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[NH4+].[Cl-]>CCO.O.[Fe]>[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[N:23]=[C:22]([NH2:24])[CH:21]=[N:20]3)[O:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 67958709HCID 67958709, compound

Product 1

HCID 67958713HCID 67958713, 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 1-(2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)cyclopropyl pivalate (150 mg, 0.45 mmol), iron powder (76 mg, 1.34 mmol) and NH4Cl (121 mg, 2.24 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 85° C. for 15 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (5.0 mL) was added followed by 1N NaOH (5.0 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (2×5 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 06: tR=0.73 min; [M+H]+=306.04.

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 (5.0 mL) was added
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with CH2Cl2 (2×5 mL)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-3d72d7505ddd44a0ac9b4c88a25ec315
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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