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

HRID 237732

반응식

HRID 237732 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ec006b5a2316419b869f56dac21cbb22
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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