Benzyl Bromide → 7-Benzyl-3-methylxanthine

HRID 323850

反応式

HRID 323850 の反応式
[OH-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][NH:9][C:8]=2[C:7](=[O:13])[NH:6][C:5]1=[O:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.CO>[CH2:15]([N:9]1[C:8]2[C:7](=[O:13])[NH:6][C:5](=[O:14])[N:4]([CH3:3])[C:12]=2[N:11]=[CH:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 706393-Methylxanthine

生成物 1

HCID 6856307-Benzyl-3-methylxanthine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

20 g (0.5 mol) of sodium hydroxide dissolved in 200 ml of water were added to a suspension of 83 g (0.5 mol) of 3-methylxanthine in 500 ml of methanol and the reaction mixture was stirred at 70° C. for one hour, then treated dropwise at the same temperature with 85.5 g (0.5 mol) of benzyl bromide and kept between 700 and 800 for 5 hours. The mixture was then cooled and filtered cold on a suction filter, the product was washed with water on the suction filter and dissolved hot in 1000 ml of 1N sodium hydroxide solution, filtered and slowly brought to pH 9.5 using 4N hydrochloric acid with stirring. The crystallizate was filtered off from the still warm solution, washed with water until chloride-free and dried in a vacuum drying oven overnight. Yield: 81.7 g (63.8% of theory); melting point: 263° C. C13H12N4O2 (MW=256.2 g/mol)

後処理

  1. waitkept between 700 and 800 for 5 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered cold on a suction
  4. filtrationfilter
  5. washthe product was washed with water on the suction
  6. filtrationfilter
  7. dissolutiondissolved hot in 1000 ml of 1N sodium hydroxide solution
  8. filtrationfiltered
  9. stirringwith stirring
  10. filtrationThe crystallizate was filtered off from the still warm solution
  11. washwashed with water until chloride-free
  12. customdried in a vacuum
  13. customdrying oven overnight

出典と根拠

ORDレコード
ord-509c10c13d0b40d4b4693ae8e2b6aa3f
出典データセット
uspto-grants-2001_04
特許番号
US06214992B1

関連ノート

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