Reference of 16369-21-4 ,Some common heterocyclic compound, 16369-21-4, molecular formula is C5H13NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A stirred solution of 2-[bis(2-chloroethyl)amino]-3,5-dinitrobenzoic acid (22) (5.00 g, 14.20 mmol) in SOCl2 (50 mL) and DMF (5 drops) was heated under reflux for 3 h, then cooled to room temperature and the excess SOCl2 was removed under reduced pressure. The resulting crude 2- [bis(2-chloroethyl)amino]-3,5-dinitrobenzoyl chloride was dissolved in THF (40 mL) and slowly added to a stirred solution of 2-(propylamino)ethanol (4.60 g, 44.63 mmol) in THF (40 mL) at -10 C. The mixture was stirred for 20 min at -10 0C, then treated with aqueous HCl (0.5 M, 40 mL) to pH ~ 3 before being extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with CH2Cl2/MeOH (99:1) to give 2-[bis(2-chloroethyl) amino]-iV-(2-hydroxyethyl)-3,5-dinitro-iJ-propylbenzamide (26) (3.73 g, 60%) as a yellow oil. 1HNMR [(CDj)2SO] (mixture of rotamers) delta 8.71, 8.68 (2dJ = 2.8 Hz, IH), 8.38, 8.24 (2dJ = 2.8 Hz, IH), 4.84, 4.80 (2tJ = 5.2 Hz, IH), 3.72-3.65 (m, 5H), 3.63-3.42 (m, 4H), 3.39-3.31 (m, 2H),3.24-3.12 (m, 2H), 1.66, 1.55 (2m, 2H), 0.94, 0.73 (2tJ = 7.4 Hz, 3H). HRMS(ESI) calcd for C16H23 Cl2N4O6 [M+H]+ m/z 437.0989: found 437.0993.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 16369-21-4, 2-(Propylamino)ethanol, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; AUCKLAND UNISERVICES LIMITED; PATTERSON, Adam, Vorn; SMAILL, Jeffrey, Bruce; DENNY, William, Alexander; WILSON, William, Robert; SYDDALL, Sophie; ASHOORZADEH, Amir; WO2010/44685; (2010); A1;,
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