Sodium Hydroxide → HCID 13458487、化合物

HRID 2290793ノート

反応式

HRID 2290793 の反応式
I.[NH:2]=[C:3]1[NH:7][CH2:6][CH2:5][NH:4]1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:17][C:18]1[CH:19]=[C:20]([N:24]=[C:25]=[O:26])[CH:21]=[CH:22][CH:23]=1.[Cl-:27].[Na+].O>C1COCC1>[ClH:27].[NH2:2][C:3]1[N:4]([C:25]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[CH:19]=2)=[O:26])[CH2:5][CH2:6][N:7]=1

参加物

7

反応物 5

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 69303m-Tolyl isocyanateHCID 57417360Sodium chloride; waterHCID 178506595HCID 178506595、化合物

生成物 1

HCID 13458487HCID 13458487、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

A suspension of 31.95 g (0.15 mole) of 2-iminoimidazolidine monohydroiodide in 400 ml THF was treated with 11.99 g (0.15 mole) 50% NaOH solution and stirred for 0.5 hour. Twenty grams of anhydrous Na2SO4 were added and the mixture stirred an additional 0.5 hour. After cooling to -20° C. (it was necessary to maintain a temperature of -20° C. at all times when in the free base form) under N2, a solution of 9.99 g (0.075 mole) of 3-methylphenyl isocyanate in 125 ml THF was added dropwise over a 3-hour period, maintaining a temperature of -20° C. The mixture was stirred an additional hour, then the inorganics were filtered off and the solvent was removed in vacuo, cold, to yield a yellow oil, which was stirred in cold brine and extracted with 3×150 ml portions of cold CH2Cl2. The combined CH2Cl2 extracts were dried over anhydrous K2CO3 and filtered. The filtrate was acidified to pH<3 with excess ethereal HCl, adding MeOH to dissolve solids which formed upon acidification. The solution was stored in a freezer overnight. The solvent and excess HCl were removed in vacuo to leave a yellow-orange oil, which solidified when washed with Et2O. The solid was recrystallized from MeOH/Et2O to yield 11.11 g of impure product which was converted to the free base and then back to the HCl salt, and recrystallized from MeOH/Et2O to yield 7.99 g (41.8%) of pure hydrochloride salt, a white solid, m.p. 195°-196.5° C. (dec.).

後処理

  1. stirringthe mixture stirred an additional 0.5 hour
  2. temperatureto maintain a temperature of -20° C. at all times when in the free base form) under N2
  3. temperaturemaintaining a temperature of -20° C
  4. stirringThe mixture was stirred an additional hour
  5. filtrationthe inorganics were filtered off
  6. customthe solvent was removed in vacuo
  7. customcold, to yield a yellow oil, which
  8. extractionextracted with 3×150 ml portions of cold CH2Cl2
  9. dry with materialThe combined CH2Cl2 extracts were dried over anhydrous K2CO3
  10. filtrationfiltered
  11. additionadding MeOH
  12. dissolutionto dissolve solids which
  13. customformed upon acidification
  14. waitThe solution was stored in a freezer overnight
  15. customThe solvent and excess HCl were removed in vacuo
  16. customto leave a yellow-orange oil, which
  17. washwashed with Et2O
  18. customThe solid was recrystallized from MeOH/Et2O

出典と根拠

ORDレコード
ord-c64c45dd33dd4edb91e435fe3309ba47
出典データセット
uspto-grants-1986_10
特許番号
US04618682

反応ノート

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