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

HRID 237732

反応式

HRID 237732 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ec006b5a2316419b869f56dac21cbb22
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

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