4,4'-DIAZIDODIPHENYL ETHANE synthesis

Yield:72695-23-9 82.8%

Reaction Conditions:

Stage #1: 4,4'-diaminodihydrostilbenewith sulfuric acid;sodium nitrite in water at 0; for 0.583333 h;
Stage #2: with sodium azide in hexane;water; for 1 h;

Steps:

4

Example 4: Synthesis 4, 4 -ETHYLENE-1, 1'-diphenylazide (IX) The schematic diagram for the synthesis of (IX) is illustrated in figure 7. To an ice cooled solution (5 °C) of 4, 4 -ETHYLENEDIANILINE (VIII) (5 g, 0.0235 mol) suspended in 11 % H2SO4 (200 ml) was added slowly over a period of 5 min, NAN02 (5 g, 0.072 mol) and the solution left stirring. After 30 min hexane (50 ML) was added to the solution and sodium azide slowly (5 g, 0.075 mol) with vigorous stirring. The hexane layer was separated after 1 h, washed with water, dried MGS04 and the filtrate evaporated in vacuo to yield 4, 4 -ETHYLENE-1, 1 - diphenylazide (IX) as a pale yellow solid (I) in 82. 8 % (mp. 77 °C). Elemental analysis found: C, 63.10, H, 4.53, N, 31.9. CL4HL2N6 requires C, 63.11, H, 4.58, N 31.80. W (VAX (E) 254 nm (2885): VMA (Nujo1)/cm-1 2112 (N3).

References:

WO2005/28423,2005,A2 Location in patent:Page/Page column 28