Hydrochloric Acid → 5-(Propan-2-yl)-1,2-oxazol-3-amine

HRID 871477

反応式

HRID 871477 の反応式
O[N:2]=[C:3]([NH2:13])[CH2:4][C:5]1([CH:10]([CH3:12])[CH3:11])OCC[O:6]1.Cl>C(O)C>[CH:10]([C:5]1[O:6][N:2]=[C:3]([NH2:13])[CH:4]=1)([CH3:12])[CH3:11]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86653514N'-hydroxy-2-(2-isopropyl-1,3-dioxolan-2-yl)acetimidamide

生成物 1

HCID 133346635-(Propan-2-yl)-1,2-oxazol-3-amine収率 68%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
120 °C

実験手順

N′-Hydroxy-2-(2-isopropyl-1,3-dioxolan-2-yl)acetimidamide (1.8 g, 9.57 mmol) was dissolved in ethanol (12 ml) and acidified to pH=1 with 37% aqueous hydrochloric acid. The mixture was subjected to microwave heating at 120° C. for 30 minutes. After concentration under reduced pressure the residue was diluted with dichloromethane, a solution of saturated sodium bicarbonate was added until the solution became basic (pH=11) and the organic layer separated. After multiple extractions of the water phase with dichloromethane, the organic layers were combined, dried (MgSO4), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (hexane/ethyl acetate 1:1) to afford 5-isopropylisoxazol-3-amine (819 mg, 68%). 1H NMR (300 MHz, CDCl3) δ 5.52 (s, 1H), 3.89 (bs, 2H), 2.96-2.91 (m, 1H), 1.27 (d, 6H); LC-MS (ESI) m/z 127 (M+H)+.

後処理

  1. concentrationAfter concentration under reduced pressure the residue
  2. additionwas diluted with dichloromethane
  3. additiona solution of saturated sodium bicarbonate was added until the solution
  4. customthe organic layer separated
  5. extractionAfter multiple extractions of the water phase with dichloromethane
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by silica gel chromatography (hexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-dd18d9e6235c4207b586b74d22d8a020
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

関連ノート

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