Formic Acid → Nitrogen mustard hydrochloride

Temperature

100 °C

Formic acid (10.0 g; 0.2 mol) and 37% formaldehyde (20 ml) were mixed in a 250 ml round-bottom flask equipped with reflux condenser. 1,5-Dichloro-3-azapentane, hydrochloride (17.0 g; 0.1 mol) was added and the solution was heated with magnetic stirring at 100° C. After 3 h the temperature was increased to 120° C. for 20 min and finally allowed to cool to room temperature before the solvent was evaporated in vacuo to afford 3 as white solid in quantitative yield. 1HNMR (CD3OD, 400 MHz) δ 3.0 (s, 3H); 3.45 (br s, 2H); 3.62 (br s, 2H); 4.07 (br s, 4H).

1. customequipped
2. temperaturewith reflux condenser
3. temperaturethe solution was heated
4. temperatureAfter 3 h the temperature was increased to 120° C. for 20 min
5. temperatureto cool to room temperature before the solvent
6. customwas evaporated in vacuo

ORD record

ord-f7b1eeb5ed8648d4bb831616f3f48124

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202993B2