Hydrochloric Acid → 1-propyl-1H-imidazol-2-amine

HRID 1612315ノート

反応式

HRID 1612315 の反応式
C1(/C=[N:8]/[C:9]2[N:10]([CH2:14][CH2:15][CH3:16])[CH:11]=[CH:12][N:13]=2)C=CC=CC=1.Cl>>[CH2:14]([N:10]1[CH:11]=[CH:12][N:13]=[C:9]1[NH2:8])[CH2:15][CH3:16]

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 22147424(E)-1-phenyl-N-(1-propylimidazol-2-yl)methanimine

生成物 1

HCID 221475261-propyl-1H-imidazol-2-amine収率 56%

実験手順

A mixture of N-[(1E)-phenylmethylidene]-1-propyl-1H-imidazol-2-amine (0.92 g, 4.31 mmol) and 6N HCl (25 mL) was heated at reflux for 2 h. After cooling to rt, the reaction was concentrated to a residue then taken up in 2M aqueous Na2CO3 and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10) to give 0.30 g (56%) of brown oil: 1H NMR (400 MHz, CDCl3) δ 6.63, 6.52, 4.00, 3.65, 1.75, 0.95; MS (ESI+) 126.7.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationthe reaction was concentrated to a residue
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10)

出典と根拠

ORDレコード
ord-2de3aff44d8c4e998845e365522a33af
出典データセット
uspto-grants-2006_01
特許番号
US06992087B2

反応ノート

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