Cyanuric chloride → 3-(4,6-Dichloro-s-triazin-2-yl)-3-azabicyclo[3.2.2]nonane

HRID 443761

反応式

HRID 443761 の反応式
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH:10]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[CH2:13][NH:12][CH2:11]2.[OH-].[Na+].C(=O)=O.CC(C)=O>O.CC(C)=O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:12]2[CH2:13][CH:14]3[CH2:17][CH2:18][CH:10]([CH2:16][CH2:15]3)[CH2:11]2)[N:7]=1

参加物

7

反応物 4

HCID 7954Cyanuric chlorideHCID 92403-Azabicyclo[3.2.2]nonaneHCID 14798Sodium HydroxideHCID 18522661Acetone cardice

生成物 1

HCID 155725793-(4,6-Dichloro-s-triazin-2-yl)-3-azabicyclo[3.2.2]nonane

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 962Water溶媒2 回

反応条件

温度
-10 °C

実験手順

Two hundred and eighty grams (1.5 mole) of cyanuric chloride is dissolved in 1.4 l. of acetone, then 1.8 l. of water is added and the mixture cooled to -10° C. using a dry-ice/acetone bath. 130 g. (1.0 mole) of 3-azabicyclo[3.2.2]nonane slurried in 200 ml. of acetone is then added all at once and the reaction is allowed to stir at -10° C. for 15 minutes. 100 ml. of 10 N NaOH is then added all at once giving rise to a small exotherm. After cooling to -10° C. using the dry-ice/acetone bath, the reaction mixture is stirred without further cooling for 3.8 hours allowing the temperature to rise to about 20° C. Two liters of water is then added, the precipitate filtered off and then washed with water. The precipitate is then dissolved in chloroform, excess water separated, the chloroform solution dried over magnesium sulfate and filtered through Magnesol®. The Magnesol® is then washed with chloroform, solvent removed in vacuo and recrystallized from dichloromethane-hexanes giving 170 g. of needles, m.p. 153°-154° C.

後処理

  1. customall at once giving rise to a small exotherm
  2. temperatureAfter cooling to -10° C.
  3. stirringthe reaction mixture is stirred
  4. temperaturewithout further cooling for 3.8 hours
  5. customto rise to about 20° C
  6. filtrationthe precipitate filtered off
  7. washwashed with water
  8. dissolutionThe precipitate is then dissolved in chloroform
  9. customexcess water separated
  10. dry with materialthe chloroform solution dried over magnesium sulfate
  11. filtrationfiltered through Magnesol®
  12. washThe Magnesol® is then washed with chloroform, solvent
  13. customremoved in vacuo
  14. customrecrystallized from dichloromethane-hexanes giving 170 g

出典と根拠

ORDレコード
ord-2075d1d3da21407ebaecfa4f04bc37d2
出典データセット
uspto-grants-1981_04
特許番号
US04261892

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