1-tert-butyl-3-(2-chloroethyl)urea

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

Procedure: A 0° C. solution of 1-(tert-butyl)-3-(2-chloroethyl)urea (2.00 g, 11.19 mmol) in THF (20 mL) was treated with NaH (60% in mineral oil, 0.800 g, 33.3 mmol), stirred at RT for 1 h, then heated at 65° C. overnight. The mixture was cooled to RT, 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-(tert-butyl)imidazolidin-2-one (1.19 g, 75%). MS (ESI) m/z: 143.1 (M+H+). heated at 65° C. overnight The mixture was cooled to RT 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 t-butylamine (6.00 g, 82 mmol) in MeCN (120 mL) was treated with 2-chloroethylisocyanate (9.00 g, 85 mmol), stirred at RT for 1 h, and the resulting solid was collected via filtration to afford 1-(tert-butyl)-3-(2-chloroethyl)urea (12.2 g, 83%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.89 (t, J=5.9 Hz, 1 H), 5.82 (s, 1 H), 3.53 (t, J=6.2 Hz, 2 H), 3.24 (q, J=6.1 Hz, 2 H), 1.19 (s, 9 H); MS (ESI) m/z: 179.1 (M+H+). the resulting solid was collected via filtration

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

Procedure: A solution of t-butylamine (6.00 g, 82 mmol) in MeCN (120 mL) was treated with 2-chloroethylisocyanate (9.00 g, 85 mmol), stirred at RT for 1 h, and the resulting solid was collected via filtration to afford 1-(tert-butyl)-3-(2-chloroethyl)urea (12.2 g, 83%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.89 (t, J=5.9 Hz, 1 H), 5.82 (s, 1 H), 3.53 (t, J=6.2 Hz, 2 H), 3.24 (q, J=6.1 Hz, 2 H), 1.19 (s, 9 H); MS (ESI) m/z: 179.1 (M+H+). the resulting solid was collected via filtration