반응 #8589

반응 방정식

nitric acid

aniline

cyanamide

→

N-phenylguanidinium nitrate

수율 32.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 3.5 hours
3. 3
   농축The mixture was concentrated in vacuo
4. 4
   기타the residue was crystallized from methanol/ethyl acetate/dichloromethane

실험 절차

To a room temperature solution of aniline (10.0 g, 107 mmol) in ethanol (100 mL) was added cyanamide (9.6 mL, 50 wt% in water, 123 mmol) followed by the dropwise addition of concentrated nitric acid (7.56 mL). The mixture was heated at reflux for 3.5 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo and the residue was crystallized from methanol/ethyl acetate/dichloromethane to yield N-phenylguanidinium nitrate (6.7 g, 32%) as a white crystalline solid. 1H NMR (DMSO-d6): δ 9.63 (s, 1 H), 7.44 (t, 2 H), 7.37 (broad s, 3 H), 7.29 (t, 1 H), 7.23 (d, 2 H); 13C NMR (DMSO-d6): δ 156.36, 135.99, 130.40, 127.19, 125.18; MS m/z 136 (M+1 of free base).

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