HCID 11051935, compound → HCID 23653020, compound

HRID 1822124Notes

Reaction equation

HRID 1822124 reaction equation
[CH:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].C([Li])CCC.C(C([O:19][N+:20]([O-])=[O:21])=O)(F)(F)F>O1CCCC1.[N+]([O-])([O-])=O.[K+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[N+:20]([O-:21])=[O:19])=[O:2]

Participants

7

Reactant 3

HCID 11051935HCID 11051935, compoundHCID 110838321H-imidazole-1-carboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 23653020HCID 23653020, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 9845Trifluoroacetic anhydrideSolventHCID 24434Potassium NitrateSolvent

Procedure

1-formyl-imidazole (about 0.100 grams) was dissolved in 1 mL of tetrahydrofuran at room temperature. Immediately, 1 equivalent (eq.) of n-butyl lithium in about 1.6 M (molar) hexanes was added to the reaction mixture, followed by 1.2 eq. of freshly prepared 1:1 molar mixture of potassium nitrate (KNO3) and trifluoroacetic anhydride (TFAA) in tetrahydrofuran as solvent at about 0° C. to about 4° C. The active nitrating species (CF3C(O)ONO2), thus, was generated in situ and the reaction mixture was stirred further for about 1.5 minutes. The 1-formyl-2-nitro-1H-imidazole product was isolated and purified by flash column chromatography to yield the pure product (i.e., about 95% purity) in about 62% yield. The structure of the 1-formyl-2-nitro-1H-imidazole product was confirmed by 1H NMR spectroscopy. 1H NMR (CDCl3): δ 2.8 (s, 3H), 7.20 (d, 1H), 7.74 (d, 1H).

Workup

  1. customof freshly prepared 1
  2. customat about 0° C. to about 4° C

Sources & evidence

ORD record
ord-9d2da05503a24f78a08612d50a55518d
Source dataset
uspto-grants-2009_10
Patent number
US07608725B2

Reaction notes

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