Triethylamine → HCID 72309473, compound

HRID 2400551Notes

Reaction equation

HRID 2400551 reaction equation
[F:1][C:2]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1.Cl.[NH2:15][OH:16].C(N(CC)CC)C>C(O)C.O>[F:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:10](=[N:15][OH:16])[NH2:11])=[CH:12][CH:13]=2)[CH2:3][O:4][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59504698HCID 59504698, compound

Product 1

HCID 72309473HCID 72309473, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(3-fluorooxetan-3-yl)benzonitrile (Step 2, 450 mg, 2.54 mmol), hydroxylamine hydrochloride (388 mg, 5.59 mmol) and triethylamine (779 μL, 5.59 mmol) in ethanol (12.5 mL) was stirred and heated at reflux over night. After being cooled to rt, the reaction mixture was diluted with water (75 mL) whereupon the product precipitated. Filtration, washing with water and drying in a vacuum oven afforded a first crop of the title compound (360 mg, 67%). A second crop was obtained after concentration of the filtrate (122 mg, 21%, purity 90%): 1H NMR (400 MHz, DMSO-d6) δ 9.71 (s, 1H), 7.77 (d, 2H), 7.54 (d, 2H), 5.87 (broad s, 2H), 4.97 (dd, 2H), 4.91 (dd, 2H); DCI(NH3)-MS m/z 211 (MH)+; HPLC RT (Method I) 2.64 min.

Workup

  1. temperatureheated
  2. temperatureat reflux over night
  3. customprecipitated
  4. filtrationFiltration
  5. washwashing with water
  6. customdrying in a vacuum oven

Sources & evidence

ORD record
ord-52e43e5bcda54b4c9287a71d5fb1945c
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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