Ammonium Hydroxide → 9H-xanthene-9-carbonitrile

HRID 393257

반응식

HRID 393257 반응식
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

참가 물질

4

반응물 3

HCID 14923Ammonium Hydroxide2회HCID 24813Phosphorus oxychlorideHCID 7255769H-Xanthene-9-carboxamide

생성물 1

HCID 133395799H-xanthene-9-carbonitrile수율 87.1%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a14edc5c6e3548f399a18b202faa31c7
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806283B2

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