2-[(4-Fluorophenoxy)methyl]oxirane → 5-(4-Fluoro-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 237732

Reaction equation

HRID 237732 reaction equation
[N:1]#[C:2][NH2:3].[Na].[F:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)=[CH:8][CH:7]=1>CO>[F:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[O:13][C:2]([NH2:3])=[N:1][CH2:14]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 27247922-[(4-Fluorophenoxy)methyl]oxiraneHCID 57375518Cyanamidnatrium

Product 1

HCID 685277115-(4-Fluoro-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamineYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vigorously stirred solution of sodium hydrogen cyanamide (0.64 g, 10.0 mmol) in methanol (10 mL) was added dropwise 2-(4-fluoro-phenoxymethyl)-oxirane (1.68 g, 10 mmol) after which the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (50 mL) was added after which the resulting white precipitate was removed by filtration through celite and the filtrate concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 0.77 g (37%) of 5-(4-fluorophenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove methanol
  3. additionAnhydrous diethyl ether (50 mL) was added after which the resulting white precipitate
  4. customwas removed by filtration through celite
  5. concentrationthe filtrate concentrated
  6. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Sources & evidence

ORD record
ord-ec006b5a2316419b869f56dac21cbb22
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Linked notes

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