ChemicalBook CAS DataBase List N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE

N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE synthesis

8synthesis methods

Product Name:N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE
CAS Number:5689-59-8
Molecular formula:C12H18ClNO
Molecular Weight:227.73

768-95-6 Synthesis

768-95-6
441 suppliers
$10.00/5g

107-14-2 Synthesis

107-14-2
286 suppliers
$15.00/25g

5689-59-8
54 suppliers
$60.00/250mg

Yield:5689-59-8 99.6%

Reaction Conditions:

Stage #1: 1-adamanthanol;chloroacetonitrilewith sulfuric acid in acetic acid;N,N-dimethyl-formamide at 20 - 80;
Stage #2: with water in acetic acid;N,N-dimethyl-formamide at 70;

Steps:

12 Example 12

A 0.50 l round-bottom three-necked flask, equipped with reflux condenser, oil ventile, mechanical stirrer, thermometer, and dropping funnel is charged with 1-hydroxyadamantane (10.00 g, 65.69 mmol), chloroacetonitrile (9.92 g, 131.38 mmol), dimethylformamide (11 ml) and acetic acid (21 ml, 363.96 mmol). The resulting suspension is slowly treated with sulphuric acid (96 %, 21 ml) at room temperature with vigorous stirring upon which the reaction mixture reaches approximately 80 °C. After completion of addition the clear reaction mixture is slowly treated with water (15 °C, 118 ml) at 70 °C. Upon ceasing of the exothermic reaction the product crystallizes. The resulting suspension is cooled to 0 - 5 °C with stirring. After filtration, the colourless crystalline solid is washed in a stream of water and dried under reduced pressure (40 °C, 19 h, 25 mbar) to yield 14.90 g (65.43 mmol, 99.60 %) of N-Adamantan-1-yl-2-chloro-acetamide. ¹H NMR (300 MHz, CDCl₃, ppm): 6.24 (b,1H, NH), 3.94 (s, 2H, RCH₂Cl), 2.10 (m, 3H, R₃CH), 2.03 (m, 6H, RCH₂R), 1.70 (m, 6H, RCH₂R). ¹³C NMR (75 MHz, DMSO-d6, ppm): δ 164.61 (CO), 52.39, 42.89, 41.37, 36.22, 29.38. MS (EI, m/z): 227 [M]⁺. IR (KBr, cm^-1): 1662 s (ν_RCONHR, Amide I), 1569 s (Amide II). mp.: 123.4 °C.