2-(Azidomethyl)-1,3-benzoxazole → 1-(1,3-Benzoxazol-2-yl)methanamine

HRID 1378722ノート

反応式

HRID 1378722 の反応式
[N:1]([CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

参加物

4

反応物 1

HCID 229128932-(Azidomethyl)-1,3-benzoxazole

生成物 1

HCID 14155281-(1,3-Benzoxazol-2-yl)methanamine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of 8.28 g (47.5 mmol) of 2-(azidomethyl)benzoxazole (PREPARATION 5) and 0.526 g of 10% Palladium on charcoal in absolute ethanol (150 ml) is shaken under hydrogen at 36 psi for 40 min. The catalyst is then filtered off and the filtrate is concentrated. The crude product is chromatographed on silica gel (700 ml) eluting with methanol/dichloromethane (2/98), the appropriate fractions are pooled and concentrated to give the product. Crystallization from ethyl ether/hexane gives the title compound, mp 46.5°-47.5°; MS (m/z) at 148; NMR (CDCl3) 1.70, 4.14, 7.33, 7.51, 7.70 δ.

後処理

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe crude product is chromatographed on silica gel (700 ml)
  4. washeluting with methanol/dichloromethane (2/98)
  5. concentrationconcentrated
  6. customto give the product
  7. customCrystallization from ethyl ether/hexane

出典と根拠

ORDレコード
ord-d7ef5936b9c54e1ebc9928d290ad8cd4
出典データセット
uspto-grants-1997_09
特許番号
US05668282

反応ノート

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