Toluene → HCID 13497235, compound

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (96 ml, 1.03 mol) is added dropwise over 30 min period to a toluene (800 ml) solution of cyclohexyl-diisopropylurea (226 g, 1.0 mol). The reaction is stirred 3.5 hours at 50° C., then stirred overnight at room temperature. Diisopropylamine (310 ml, 2.18 mol) is added to the reaction mixture dropwise for over a 2 hour period, then stirred 2 hours at room temperature. The reaction mixture is poured into water (2000 ml). The water layer is extracted with toluene (3×150 ml) and the toluene layer is discarded. Sodium hydroxide (240 g, 6 mol) is slowly added to the aqueous layer in an ice-water bath. Two layers formed and the aqueous layer is extracted with diethylether (2×150 ml). The organic layer and the extracts are combined and dried over Na2 CO3, filtered and concentrated. The residue is further distilled under vacuum (ca. 0.3-0.5 torr) collecting product, cyclohexyl-tetraisopropylguanidine, at 140°-143° C. (250g, 80%) of 99% purity as judged by gas chromatography. 1H NMR (CDCl3) δ 3.75-3.9(m, 1H), 3.37(m, 1H), 3.22-3.31 (m,1H), 1.12-1.77 (m, 10H), 1.22 (d, 6H), 1.14 (d, 6H) ppm.

Provenance & Evidence