反応 #4587

反応方程式

1-Adamantanecarbonyl chloride

sodium cyanamide

→

4

収率 85.2%

1-Adamantanecarbonyl Cyanamide

収率 85.2%

溶媒

THF

THF

反応条件

後処理

1. 1
   抽出The reaction mixture was then extracted with ethyl acetate (100 ml)
2. 2
   抽出extracted with ethyl acetate (3×60 ml)
3. 3
   抽出The ethyl acetate extract
4. 4
   乾燥was dried over anhydrous sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他the filtrate was evaporated in vacuo to dryness
7. 7
   workup.DISTILLATIONThe resulting white solid residue was triturated in a minimal amount of distilled water
8. 8
   ろ過filtered
9. 9
   その他air-dried

実験手順

1-Adamantanecarbonyl chloride (1.99 g, 0.010 mol) in 50 ml of THF was added drop-wise to a suspension of sodium cyanamide (1.92 g, 0.030 mol) in 100 ml of THF with stirring at ice bath temperature. The reaction was allowed to proceed at 25° C. for 15 hours. The reaction mixture was then extracted with ethyl acetate (100 ml). The separated aqueous portion (pH 10.5) was acidified to pH 1.5 with 10% HCl and extracted with ethyl acetate (3×60 ml). The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated in vacuo to dryness. The resulting white solid residue was triturated in a minimal amount of distilled water, filtered, and air-dried to give 1.74 g (85.2% yield) of crude 4 as white solid. This was recrystallized from ethyl acetate and petroleum ether to give 0.55 g (crop 1) of white crystalline powder. The filtrate was concentrated when further crystallization occurred to give 0.49 g (crop 2) of additional product giving a total yield of 50.9%, mp 168°-170° C. TLC: Rf =0.58 in EtOAc/petroleum ether/AcOH (50:100:1), detected by UV quenching (weak) and reddish orange color with ferricyanide spray reagent; IR (Nujol, cm-1), 3210 (NH), 2230 (C≡N), 1710 (C=O); NMR (Silanor C, δ from TMS) 1.62-2.2 (m, aliphatic CH's). Anal. Calcd for C12H16N2O: C, 70.56; H, 7.90; N, 13.71. Found: C, 70.59; H, 8.04; N, 13.66.

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