Hydrochloric Acid → HCID 10631479, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-bis(chloromethyl)-2,4,6-trimethylbenzene (10 g, 46 mmol) in DMSO (30 mL) was added sodium cyanide (2.25 g, 46 mmol). The mixture was stirred at rt overnight before sodium azide (4.5 g, 69 mmol) was added. The mixture was heated at 80° C. for 3 h before it was poured into water (300 mL). The resulting precipitate was filtered to give a 2:1:1.5 mixture of 3-cyanomethyl-2,4,6-trimethylbenzyl azide, 1,3-bis(cyanomethyl)-2,4,6-trimethylbenzene and 1,3-bis(azidomethyl)-2,4,6-trimethylbenzene. This mixture was not separated but was treated with triphenylphosphine (18 g, 69 mmol) in wet THF. The reaction was conducted and worked up as in Example 12 (procedure A) only that the HCl solution was basified with K2CO3 until no more gas evolution observed. The mixture was extracted with dichloromethane and concentrated to give only the desired 3-cyanomethyl-2,4,6-trimethylbenzylamine (2 g, 25% yield).

Provenance & Evidence