Nitrogen → HCID 67365427, compound

HRID 42820Notes

Reaction equation

HRID 42820 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:16][N:15]=[C:14]([C:17](=[O:19])[CH3:18])[CH:13]=2)[N:7]=1)([O-:5])=[O:4].COC([O:25][CH3:26])OC.[C:27]([O-])(O)=O.[Na+]>C(O)CO>[CH3:18][C:17]1([C:14]2[CH:13]=[C:12]([CH2:11][N:8]3[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]3)[O:16][N:15]=2)[O:25][CH2:26][CH2:27][O:19]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 67365635HCID 67365635, compound

Product 1

HCID 67365427HCID 67365427, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[5-(4-nitro-[1,2,3]triazol-2-ylmethyl)-isoxazol-3-yl]-ethanone (122 mg, 0.51 mmol) in ethylene glycol (0.57 mL) was treated with trimethylorthoformate (0.11 mL, 1.03 mmol) followed by LiBF4 (10 mg, 0.10 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (10 mL) was added and the mixture was extracted with EA (2×10 mL). The combined org. extracts were washed with brine (2×10 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 EA-Hept) gave the title compound as a yellow oil. TLC:rf (40:60 EA-Hept)=0.26. LC-MS-conditions 02: tR=0.89 min.

Workup

  1. extractionthe mixture was extracted with EA (2×10 mL)
  2. washextracts were washed with brine (2×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (40:60 EA-Hept)

Sources & evidence

ORD record
ord-57e71bf10f644a0f9d8323f991468d62
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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