Trifluoroacetamide → HCID 178518703、化合物

HRID 1392112ノート

反応式

HRID 1392112 の反応式
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=O.Cl.N[C:10]1[NH:14][CH:13]=[N:12][C:11]=1[C:15]([NH2:17])=[O:16]>CO>[F:1][C:2]([F:7])([F:6])[C:3]1[NH:17][C:15](=[O:16])[C:11]2[N:12]=[CH:13][NH:14][C:10]=2[N:5]=1

参加物

4

反応物 2

HCID 67717Trifluoroacetamide2 回HCID 178479549HCID 178479549、化合物

生成物 1

HCID 178518703HCID 178518703、化合物収率 65.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
110 °C

実験手順

A 1 L round-bottom flask (three neck) containing 340 g of trifluoroacetamide was heated in an oil bath at 110° C. After the trifluoroacetamide melted, 50 g of 5-aminoimidazole-4-carboxamide-HCl was added. The mixture was warmed to reflux (bath temp 160 to 165° C.) for 4 hours, cooled to room temperature, and the rocky solid was triturated with 1 L of ether. The ether was decanted off and the remaining solid was warmed until melted and 200 mL of ether was introduced by a dropping-funnel through a water-cooled condenser. The mixture was cooled to room temperature and an additional 200 mL of ether was added with stirring. The solid was removed by filtration, triturated with 3×500 mL of ether, washed with 200 mL of H2O, and filtered to provide 89 g of crude product. The product was treated with 3 L of MeOH and 9 g of activated carbon, warmed to reflux for 20 minutes, filtered through a pad of celite, and concentrated to a volume of 2.5 L. The material was warmed to dissolve all the precipitate that formed and then cooled slowly to room temperature. The crystalline material was isolated by filtration and dried in vacuo to provide 41 g of the desired hypoxanthine as a white solid. 1H NMR (DMSO-d6) δ 8.34 (s, 1H), 7.18 (bs, 2H). MS (ES+), 205.0 (100%, M+H).

後処理

  1. temperatureThe mixture was warmed
  2. temperatureto reflux (bath temp 160 to 165° C.) for 4 hours
  3. temperaturecooled to room temperature
  4. customthe rocky solid was triturated with 1 L of ether
  5. customThe ether was decanted off
  6. temperaturethe remaining solid was warmed
  7. addition200 mL of ether was introduced by a dropping-funnel through a water-
  8. temperaturecooled condenser
  9. temperatureThe mixture was cooled to room temperature
  10. additionan additional 200 mL of ether was added
  11. customThe solid was removed by filtration
  12. customtriturated with 3×500 mL of ether
  13. washwashed with 200 mL of H2O
  14. filtrationfiltered
  15. customto provide 89 g of crude product
  16. temperaturewarmed
  17. temperatureto reflux for 20 minutes
  18. filtrationfiltered through a pad of celite
  19. concentrationconcentrated to a volume of 2.5 L
  20. temperatureThe material was warmed
  21. dissolutionto dissolve all the precipitate
  22. customthat formed
  23. temperaturecooled slowly to room temperature
  24. customThe crystalline material was isolated by filtration
  25. customdried in vacuo

出典と根拠

ORDレコード
ord-7418b29759f04cc2949e866df54d4642
出典データセット
uspto-grants-2008_03
特許番号
US07342021B2

反応ノート

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