反应详情

Chloroethylisocyanate (Compound 5, Aldrich, 346 mg, 3.3 mmol) was added to a stirred solution of 2,3-dimethylaniline (Aldrich, 400 mg, 3.3 mmol) in tetrahydrofuran (5 ml) at room temperature. After 30 minutes a white precipitate formed. The solid chloroethylurea was collected by vacuum filtration yield: 477 mg (64%): mp 145°-146° C. HNMR (300 MHz, CDCl3) σ 7.00 (m, 3H); 6.72 (br, 1H); 5.19 (br, 1H), 3.59 (m, 2H); 3.49 (m, 2H); 2.30 (s, 3H); 2.18 (s, 3H); Mass spectrum m/e 226.0872 (C1H15ClN2O requires 226.0872). The chlorethylurea (199 mg, 0.88 mmol) was suspended in H2O (4 ml) and CH3OH (4 ml) and heated to reflux for 1 hour. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with 1N NaOH (to pH 13). The organic layer was dried over Na2CO3 and concentrated in vacuo to yield 140 mg (84%) of the title compound as a white crystalline solid: mp 112°-113.5° C.; 1H NMR (300 MHz, CDCl3) σ 7.19 (m, 1H); 7.09 (m, 1H), 6.91 (m, 1H); 5.00 (br, s, 1H); 4.40 (t, 2H); 3.70 (t, 2H); 2.30 (s, 3H); 2.15 (s, 3H); Mass spectrum m/e 190.1104 (C11H14N2O requires 190.1106).

1. customAfter 30 minutes a white precipitate formed
2. filtrationThe solid chloroethylurea was collected by vacuum filtration yield: 477 mg (64%)
3. temperatureto reflux for 1 hour
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in CH2Cl2
6. washwashed with 1N NaOH (to pH 13)
7. dry with materialThe organic layer was dried over Na2CO3
8. concentrationconcentrated in vacuo