Hydrochloric Acid → 5-Hydroxy-5-(5-bromo-3-indolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

HRID 1285153

反応式

HRID 1285153 の反応式
O.[NH:2]1[C:10](=[O:11])[C:8](=[O:9])[C:6](=[O:7])[NH:5][C:3]1=[O:4].[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2.Cl>C(O)C>[OH:9][C:8]1([C:16]2[C:15]3[C:19](=[CH:20][CH:21]=[C:13]([Br:12])[CH:14]=3)[NH:18][CH:17]=2)[C:6](=[O:7])[NH:5][C:3](=[O:4])[NH:2][C:10]1=[O:11]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrateHCID 249055-Bromoindole

生成物 1

HCID 132828955-Hydroxy-5-(5-bromo-3-indolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione収率 93.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Alloxan hydrate (1.6 g., 0.01 mole) was dissolved in 40 ml. of ethanol by heating. 5-Bromoindole (1.96 g., 0.01 mole) was added and heating near reflux continued for 15 minutes. Tlc did not indicate that reaction had occured. 1N Hydrochloric acid (10 ml.) was then added while maintaining the reaction near reflux. After 10 minutes, the reaction was concentrated to wet solids. Trituration of these wet solids with water gave the title product [3.17 g., m.p. >250° C.; Rf 0.45 (1:1 ethyl acetate:hexane/5% acetic acid); Rf 0.3 (1:5 ethyl acetate:hexane/5% acetic acid)].

後処理

  1. temperatureheating
  2. temperaturenear reflux
  3. customTlc did not indicate that reaction
  4. temperaturewhile maintaining
  5. customthe reaction
  6. temperaturenear reflux
  7. waitAfter 10 minutes
  8. concentrationthe reaction was concentrated to wet solids

出典と根拠

ORDレコード
ord-cb67ba3afd044b3f87410c30490bf3ac
出典データセット
uspto-grants-1986_01
特許番号
US04565820

関連ノート

読み込み中…