反応 #4589

反応方程式

Stearoyl chloride

sodium cyanamide

charcoal

→

Stearoylcyanamide

収率 92.4%

溶媒

THF

THF

—

EtOAc petroleum ether AcOH

反応条件

後処理

1. 1
   workup.ADDITIONwas added drop-wise
2. 2
   workup.DISTILLATIONof freshly distilled dry THF with vigorous stirring
3. 3
   その他The solids which formed
4. 4
   ろ過were collected by filtration
5. 5
   ろ過filtered
6. 6
   その他air-dried
7. 7
   その他to give 2.85 g (92.4% yield) of crude 7
8. 8
   濃縮The filtrate was concentrated until the solution
9. 9
   workup.ADDITIONAddition of petroleum ether
10. 10
    その他gave 2.29 g (crop 1) of white waxy 7
11. 11
    濃縮The filtrate was concentrated
12. 12
    workup.ADDITIONpetroleum ether added
13. 13
    その他to give 0.28 g (crop 2) of additional product
14. 14
    その他giving a total yield of 83.3%, mp 74°-75 ° C
15. 15
    その他quenching (weak)
16. 16
    その他no color reaction with ferricyanide spray reagent

実験手順

Stearoyl chloride (3.03 g, 0.010 mol) in 50 ml of freshly distilled dry THF was added drop-wise to a suspension of sodium cyanamide (1.92 g, 0.030 mol) in 100 ml of freshly distilled dry THF with vigorous stirring. The reaction was allowed to proceed at 25° C for 63 hours. The solids which formed were collected by filtration and the solid cake was suspended in 200 ml of distilled water. The resulting soapy suspension (pH 10.5) was acidified to pH 1.5 with 10% HCl, filtered, and air-dried to give 2.85 g (92.4% yield) of crude 7. This was dissolved in THF and the solution decolorized with activated charcoal. The filtrate was concentrated until the solution became turbid. Addition of petroleum ether gave 2.29 g (crop 1) of white waxy 7. The filtrate was concentrated and petroleum ether added to give 0.28 g (crop 2) of additional product giving a total yield of 83.3%, mp 74°-75 ° C. TLC: Rf =0.69 in EtOAc/petroleum ether/AcOH (50:100:1), detected by UV quenching (weak) and no color reaction with ferricyanide spray reagent; IR (Nujol, cm-1) 3210 (NH), 2250 (C≡N), 1735 (C=O); NMR (Silanor C, δ from TMS) 2.3-2.6 (t, --CH2 --CH2 --C=O), 1.0-1.8 (fused s, (CH2)14), 0.8-0.9 (t, CH3 --CH2 --); Anal. Calcd for C19H36N2O: C, 73.97; H, 11.76; N, 9.08. Found: C, 73.88; H, 11.50; N, 9.09.

出典