Guanidine Hydrochloride → 10065-79-9

Participants

Reaction Conditions

Reaction Steps

Dichloromethane (80 ml) is added to a solution of guanidine hydrochloride (3.82 g, 40 mmol) and sodium hydroxide (8 g, 0.2 mol) in water (40 ml) and the resulting mixture is cooled to 0° C. Benzyloxycarbonyl chloride (17.1 ml, 120 mmol) is added dropwise with vigorous stirring over a period of 45 min. After the addition is completed, stirring is continued for 20 h at 0° C. The mixture is diluted with dichloromethane (100 ml), the layers are separated and the aqueous layer is extracted with dichloromethane (100 ml). The extracts are combined, washed with water and dried with magnesium sulfate. After filtering and removal of the solvent under reduced pressure the crude product is recrystallized from methanol. N-,N′-Di-Cbz-guanidine (9.85 g, 75%) is obtained as colorless crystals: mp: 149-150° C.; 1H NMR (360 MHz, DMSO-d6) δ 10.88 (br s, 1H), 8.67 (br s, 2H), 7.40-7.25 (m, 10H), 5.10 (s, 4H); Anal. Calc. for C, 62.38%; H, 5.23%;.N, 12.84%. Found: C, 62.26%; H, 5.01%;.N, 12.79%.

Provenance & Evidence