ChemicalBook CAS DataBase List 4-TOLYLISOCYANIDE

4-TOLYLISOCYANIDE synthesis

11synthesis methods

Product Name:4-TOLYLISOCYANIDE
CAS Number:7175-47-5
Molecular formula:C8H7N
Molecular Weight:117.1479

To a flask containing 5.4 gm (0.05 mole) of p-toluidine in 100 ml of dry 1,2-dimethoxyethane is added 28 gm (0.15 mole) of sodium trichloroacetate. The reaction is slightly exothermic. The reaction mixture is refluxed for ? hr, whereupon carbon dioxide is copiously evolved. The reaction mixture is filtered, the solid (10 gm) is washed with ether, and the combined reddish black filtrate concentrated. The residue is extracted with ether, washed with water, dried, and concentrated to afford a red-black oil, which, upon distillation, gives 2.5 gm (43%), b.p. 38°C (1 mm Hg), m.p. 19-20°C of a yellow liquid, IR, 4.69 μ (—NC).
Preparation ofp-Tolyl Isonitrile

3085-54-9 Synthesis

3085-54-9
59 suppliers
$39.89/250mg

7175-47-5
9 suppliers
inquiry

Yield:7175-47-5 95%

Reaction Conditions:

with diisopropylamine;trichlorophosphate in dichloromethane at 0 - 20;Inert atmosphere;

Steps:

Representative procedure for the synthesis of isonitriles: Compound (2g)

To a stirring 0 °C mixture of DIPA (2.7 equiv, 3.9 mL) and N-(3-bromophenyl)formamide (2.06 g) in DCM (0.9 M), as added POCl3 (1.1 equiv, 1.06 mL) dropwise under argon. After 5 min at 0°C and 15 min at room temperature, 10 mL water was added and mixed vigorously until the organic layer became clear. The organic layer was separated, loaded onto a short silica gel flash column, and eluted with 4:1 hexanes:ethyl acetate to give 1.53 g (81%) of a foul-smelling yellow liquid which became dark green after drying in vacuo 10 min.

References:

Polisar, Jason G.;Li, Ling;Norton, Jack R. [Tetrahedron Letters,2011,vol. 52,# 23,p. 2933 - 2934] Location in patent:supporting information; experimental part

67-66-3 Synthesis