Triethylamine → 4-(2-fluoropropan-2-yl)-N'-hydroxybenzenecarboximidamide

HRID 2400555Notes

Reaction equation

HRID 2400555 reaction equation
[F:1][C:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].Cl.[NH2:14][OH:15].C(N(CC)CC)C>C(O)C>[F:1][C:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9](=[N:14][OH:15])[NH2:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 595046394-(2-Fluoropropan-2-yl)benzenecarbonitrile

Product 1

HCID 723094744-(2-fluoropropan-2-yl)-N'-hydroxybenzenecarboximidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(2-fluoropropan-2-yl)benzonitrile (Step 1, 675 mg, 4.14 mmol), hydroxylamine hydrochloride (632 mg, 9.10 mmol) and triethylamine (1.27 mL, 9.10 mmol) in ethanol (20 mL) was stirred and heated at reflux for 1 h. After being cooled to rt, the reaction mixture was evaporated to dryness. The resulting material was treated with ethyl acetate and the solid was filtered off. The ethyl acetate solution was washed with water and saturated sodium chloride solution, dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the title compound was obtained (756 mg, 93%): 1H NMR (400 MHz, CDCl3) δ 7.62 (d, 2H), 7.41 (d, 2H), 4.89 (broad s, 2H), 1.72 (s, 3H), 1.68 (s, 3H); ES-MS m/z 197, HPLC RT (Method F) 1.04 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customthe reaction mixture was evaporated to dryness
  4. additionThe resulting material was treated with ethyl acetate
  5. filtrationthe solid was filtered off
  6. washThe ethyl acetate solution was washed with water and saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-6b71c311e7e7467981c581c56450571b
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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