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Hydrochloric Acid → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(2-chloro-3,4-dimethoxyphenyl)ethenyl)-1,3-dimethyl-, (E)-

HRID 1077495
ノート
印刷プレビュー

反応式

HRID 1077495 の反応式
[Cl:1][C:2]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](O)=O.S(Cl)(Cl)=O.[NH2:21][C:22]1[C:23](=[O:32])[N:24]([CH3:31])[C:25](=[O:30])[N:26]([CH3:29])[C:27]=1[NH2:28].Cl>N1C=CC=CC=1.[OH-].[Na+].O1CCOCC1.O.C(Cl)Cl>[Cl:1][C:2]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6]1[NH:21][C:22]2[C:23](=[O:32])[N:24]([CH3:31])[C:25](=[O:30])[N:26]([CH3:29])[C:27]=2[N:28]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 795015,6-Diamino-1,3-dimethyluracilHCID 27749672-Chloro-3,4-dimethoxycinnamic acid

生成物 1

HCID 64488901H-Purine-2,6-dione, 3,7-dihydro-8-(2-(2-chloro-3,4-dimethoxyphenyl)ethenyl)-1,3-dimethyl-, (E)-収率 30%

試薬・触媒・溶媒 5

HCID 962
Water
溶媒
HCID 1049Pyridine溶媒
HCID 6344Dichloromethane溶媒
HCID 14798Sodium Hydroxide溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

2-Chloro-3,4-dimethoxycinnamic acid (3.93 g, 16.2 mmol) was dissolved in 57 ml of pyridine. To the solution was added 1.26 ml (17.6 mmol) of thionyl chloride under ice cooling, and the mixture was stirred at 60° C. for 1.5 hours. Methylene chloride (58 ml) containing 2.50 g (14.7 mmol) of 5,6-diamino-1,3-dimethyluracil was added dropwise to the solution under ice cooling, and the reaction solution was stirred at room temperature for further 40 minutes. The deposited crystals were collected by filtration and the obtained crude crystals were dissolved in a mixture of 68 ml of an aqueous 2N sodium hydroxide solution, 68 ml of dioxane, and 34 ml of water, followed by heating under reflux for 30 minutes. After cooling, the solution was neutralized with a concentrated aqueous solution of hydrochloric acid, and the deposited crystals were collected by filtration. The collected crystals were washed with water, dried, and recrystallized from dimethylformamide/water to give 1.55 g (yield 30%) of Compound 107 as pale yellow needles.

後処理

  1. additionwas added dropwise to the solution under ice cooling
  2. stirringthe reaction solution was stirred at room temperature for further 40 minutes
  3. filtrationThe deposited crystals were collected by filtration
  4. customthe obtained crude crystals
  5. temperatureby heating
  6. temperatureunder reflux for 30 minutes
  7. temperatureAfter cooling
  8. filtrationthe deposited crystals were collected by filtration
  9. washThe collected crystals were washed with water
  10. customdried
  11. customrecrystallized from dimethylformamide/water

出典と根拠

ORDレコード
ord-c85c8b8a2ea24794a64f06132807e690
出典データセット
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05543415

反応ノート

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