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

HRID 631432노트

반응식

HRID 631432 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
120 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca7a53d0849545f28aa7318a67e8f941
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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