1-Adamantanecarbonyl chloride → 1-Adamantanecarbonyl Cyanamide

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.

1. extractionThe reaction mixture was then extracted with ethyl acetate (100 ml)
2. extractionextracted with ethyl acetate (3×60 ml)
3. extractionThe ethyl acetate extract
4. dry with materialwas dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customthe filtrate was evaporated in vacuo to dryness
7. distillationThe resulting white solid residue was triturated in a minimal amount of distilled water
8. filtrationfiltered
9. customair-dried

ORDレコード

ord-8d2f5af8638c4353be74f64ba58b6a7f

出典データセット

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04726941