1-(2-chloroethyl)-3-propan-2-ylurea

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0° C. suspension of 1-(2-chloroethyl)-3-isopropylurea (6.00 g, 36.4 mmol) in THF (60 mL) was treated with NaH (60% in mineral oil, 2.50 g, 104 mmol) and stirred at RT overnight. The mixture was concentrated to dryness, treated with satd. NH4Cl, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 1-isopropylimidazolidin-2-one (3.21 g, 69%) as a waxy solid. MS (ESI) m/z: 129.1 (M+H+). The mixture was concentrated to dryness treated with satd NH4Cl, extracted with EtOAc (3×) the combined organics were dried over Na2SO4 concentrated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of isopropylamine (3.00 g, 50.8 mmol) in MeCN (30 mL) was treated with 2-chloroethylisocyanate (6.00 g, 56.9 mmol), stirred at RT for 1 h and the resulting solid collected via filtration to afford 1-(2-chloroethyl)-3-isopropylurea (6.12 g, 73%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.96 (t, J=5.9 Hz, 1 H), 5.87 (d, J=7.7 Hz, 1 H), 3.62 (m, 1 H), 3.53 (t, J=6.3 Hz, 2 H), 3.25 (m, 2 H), 0.99 (d, J=6.5 Hz, 6 H); MS (ESI) m/z: 165.1 (M+H+). the resulting solid collected via filtration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of isopropylamine (3.00 g, 50.8 mmol) in MeCN (30 mL) was treated with 2-chloroethylisocyanate (6.00 g, 56.9 mmol), stirred at RT for 1 h and the resulting solid collected via filtration to afford 1-(2-chloroethyl)-3-isopropylurea (6.12 g, 73%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.96 (t, J=5.9 Hz, 1 H), 5.87 (d, J=7.7 Hz, 1 H), 3.62 (m, 1 H), 3.53 (t, J=6.3 Hz, 2 H), 3.25 (m, 2 H), 0.99 (d, J=6.5 Hz, 6 H); MS (ESI) m/z: 165.1 (M+H+). the resulting solid collected via filtration