Ethylamine → (3-Ethylcarbamoyl-propyl)-carbamic acid tert-butyl ester

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Reaction Steps

An aqueous solution of ethylamine (70%, 41 ml) was added into an ice cold solution of benzotriazole derivative 2 (50 g, 156 mmol) in CH2Cl2 (500 ml), stirred for 1 h at room temperature, diluted 2 times with CH2Cl2, washed with H2O, then brine, dried (Na2SO4), concentrated and dried in vacuo. Yield 32.845 g (91%). mp: 82-83° C. 1H NMR (CDCl3): 1.15 (t, J=7.27, 3H), 1.44 (s, 9H), 1.75-1.85 (m, 2H), 2.20 (t, J=7.10, 2H), 3.17 (q, J=6.49, 2H), 3.24-3.34 (m, 2H), 4.82 (s, 1H), 6.13 (bs, 1H). 13C NMR (CDCl3): 14.72, 24.91, 26.33, 28.35, 33.66, 33.92, 34.32, 39.78, 79.21, 156.44, 172.43. ESI-MS: 483.4 (M2Na+), 461.4 (M2H+), 321.2 (MH+).

Provenance & Evidence