1,1′-(1,2-Diazenediyl)bis[1-(4-morpholinyl)methanone]

To a stirred solution of diethyl azodicarboxylate(40 wtpercent in toluene; 5 mL, 11.5 mmol, 1 equiv) in Et2O (25 mL) at 0 C wasadded a solution of morpholine (1.98 mL, 23 mmol, 2 equiv) in Et2O (25 mL)over 3 h with a dropping funnel. The reaction mixture was stirred for afurther 2 h whilst slowing warming to room temperature. The yelloworangeprecipitate was collected by vacuum filtration, washed with coldEt2O, and dried on the filter to furnish ADDM as a yellow-orange solid (1.62 g, 55percent yield): dH (CDCl3, 400 MHz) 3.61 (m, 4H, 2CH2), 3.74 (m, 8H, 4CH2), 3.83(m, 4H, 2CH2).To a solution ofdiethyl ether (30 mL) and morpholine (2.50 mL, 2.87 mmol) wasadded diethylazodicarboxylate (1.79 mL, 11.5 mmol) dropwise at 0 C, and stirred for 30 min, after which a light orange precipitate fell out ofsolution. The precipitate was filtered, washed with diethyl ether anddried under vacuum to afford the product as a light orange solid. 2.63 g, 89% yield. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.58-3.66 (m, 4H), 3.68-3.80 (m, 8H), 3.81-3.86 (m, 4H); 13C NMR; (75 MHz, CHLOROFORM-d) delta ppm 43.7, 45.2, 66.4, 66.5, 110.0, 159.7.Characterization data corresponded with available literature values.23To a stirred solution of diethyl azodicarboxylate(40 wt% in toluene; 5 mL, 11.5 mmol, 1 equiv) in Et2O (25 mL) at 0 C wasadded a solution of morpholine (1.98 mL, 23 mmol, 2 equiv) in Et2O (25 mL)over 3 h with a dropping funnel. The reaction mixture was stirred for afurther 2 h whilst slowing warming to room temperature. The yelloworangeprecipitate was collected by vacuum filtration, washed with coldEt2O, and dried on the filter to furnish

Reagent for synthesizing symmetric and asymmetric disulfides in polar solvents (such as water)

Molecular Weight:256.26
XLogP3:-0.6
Hydrogen Bond Acceptor Count:4
Exact Mass:256.11715500
Monoisotopic Mass:256.11715500
Topological Polar Surface Area:83.8
Heavy Atom Count:18
Complexity:303
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes