Nitrogen → 1-(5-Fluoro-hexyl)-4-nitro-1H-pyrazole

HRID 2064948Notes

Reaction equation

HRID 2064948 reaction equation
N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH:15](O)[CH3:16])[CH:10]=1)([O-:5])=[O:4].[F:18]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.F.F.F.C(N(CC)CC)C>C1COCC1.CCN(CC)CC>[F:18][CH:15]([CH3:16])[CH2:14][CH2:13][CH2:12][CH2:11][N:9]1[CH:10]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[N:8]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 669286716-(4-Nitro-pyrazol-1-yl)-hexan-2-ol

Product 1

HCID 669284931-(5-Fluoro-hexyl)-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 6-(4-nitro-pyrazol-1-yl)-hexan-2-ol (213 mg, 1.00 mmol) in THF (3.0 mL) was treated at rt with perfluoro-1-butanesulfonyl fluoride (0.36 mL, 2.00 mmol), triethylamine trihydrofluoride (0.33 mL, 2.00 mmol) and Et3N and the reaction mixture was stirred at rt overnight. Purification of the residue by FC (80:10 hept-EA) gave the title compound. TLC: rf (80:20 hept-EA)=0.28. LC-MS-conditions 02: tR=0.97 min; [M+H]+=216.20.

Workup

  1. customPurification of the residue by FC (80:10 hept-EA)

Sources & evidence

ORD record
ord-951d4960fb79417bac4b5b89f3345ec0
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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