Ammonium Hydroxide → 9H-xanthene-9-carbonitrile

HRID 393257

反応式

HRID 393257 の反応式
O=P(Cl)(Cl)Cl.[CH:6]1[C:19]2[CH:18]([C:20]([NH2:22])=O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[NH4+].[OH-]>>[CH:16]1[C:17]2[CH:18]([C:20]#[N:22])[C:19]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:11][C:12]=2[CH:13]=[CH:14][CH:15]=1

参加物

4

反応物 3

HCID 14923Ammonium Hydroxide2 回HCID 24813Phosphorus oxychlorideHCID 7255769H-Xanthene-9-carboxamide

生成物 1

HCID 133395799H-xanthene-9-carbonitrile収率 87.1%

実験手順

POCl3 (25 mL) was added to crystalline 9H-Xanthene-9-carboxamide [26] (1.5 g, 6.65 mmol) while stirring. The solution was then heated at reflux (45 min), when TLC showed complete absence of starting material. The solution was then poured into a mixture of crushed ice and NH4OH with vigorous stirring. The solution was stirred (15 min) and excess of NH4OH was added to keep the solution alkaline. The solid formed was extracted with ether (3×50 ml). The combined ether extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure to give an yellow oil which crystallized immediately. The product was purified by mplc using pet. ether: acetone (8:2) as eluent to give 1.2 g (87%) 9H-Xanthene-9-carbonitrile as colorless needles, mp 97-98° C. (EtOH).

後処理

  1. temperatureThe solution was then heated
  2. temperatureat reflux (45 min), when TLC
  3. stirringThe solution was stirred (15 min)
  4. customThe solid formed
  5. extractionwas extracted with ether (3×50 ml)
  6. washThe combined ether extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto give an yellow oil which
  10. customcrystallized immediately
  11. customThe product was purified by mplc

出典と根拠

ORDレコード
ord-a14edc5c6e3548f399a18b202faa31c7
出典データセット
uspto-grants-2004_10
特許番号
US06806283B2

関連ノート

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