Pyridine → HCID 86680494, compound

HRID 1777467Notes

Reaction equation

HRID 1777467 reaction equation
[OH:1][NH:2][C:3](=[NH:6])[CH2:4][OH:5].[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=O)=[CH:10][CH:9]=1.N1C=CC=C[CH:18]=1>C(Cl)Cl>[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]2[O:1][N:2]=[C:3]([CH:4]([OH:5])[CH3:18])[N:6]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 178511448HCID 178511448, compound

Product 1

HCID 86680494HCID 86680494, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,2-dihydroxyacetimidamide (2.7 g, 26.4 mmol) in pyridine (20 mL) was added dropwise 4-fluorobenzoyl chloride (3 g, 18.9 mmol) in DCM (30 mL) at 0° C. to 10° C. The reaction was stirred for 6 hours at room temperature and the solid was filtered and washed with DCM (50 mL). The solid was dissolved in ethanol and the solution refluxed for 16 hours at 85° C. The mixture was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (100-200 mesh; using 10% ethyl acetate in hexane) to obtain 1-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)ethanol as white solid (0.35 g, 9% yield). 1H NMR (400 MHz, CDCl3): δ 8.14 (dd, 1H), 7.20 (dd, 1H), 5.06 (q, 1H), 1.66 (d, 3H).

Workup

  1. filtrationthe solid was filtered
  2. washwashed with DCM (50 mL)
  3. dissolutionThe solid was dissolved in ethanol
  4. temperaturethe solution refluxed for 16 hours at 85° C
  5. customThe mixture was evaporated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography (100-200 mesh; using 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-52a422e2a4de49b2a0bd564df9034034
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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