ChemicalBook CAS DataBase List 2-chloro-10-(3-chloropropyl)-10H-phenothiazine

2-chloro-10-(3-chloropropyl)-10H-phenothiazine synthesis

5synthesis methods

Product Name:2-chloro-10-(3-chloropropyl)-10H-phenothiazine
CAS Number:2765-59-5
Molecular formula:C15H13Cl2NS
Molecular Weight:310.24

92-39-7 Synthesis

92-39-7
384 suppliers
$14.00/5g

109-70-6 Synthesis

109-70-6
483 suppliers
$10.00/5g

2-chloro-10-(3-chloropropyl)-10H-phenothiazine

2765-59-5
32 suppliers
$280.00/250MG

Yield:2765-59-5 93%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide at 0 - 20; for 2 h;

Steps:

2-Chloro-10-(3-chloropropyl)-10H-phenothiazine (5)

Toa suspension of sodium hydride (NaH) (55% (w/w)), 542 mg,12.4 mmol) in N,N-dimethylformamide (DMF) (4.1 mL)were added chlorophenothiazine 4 (1.00 g, 4.28 mmol) and1-bromo-3-chloropropane (890μL, 8.99 mmol) at 0°C, andthe obtained suspension was stirred at room temperaturefor 2 h. After quenching by the addition of brine at 0°C, themixture was extracted with Et2O. Following to washing withwater (3 times), the combined organic layer was dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by column chromatography (hexane-EtOAc=100 : 1(v/v)), and alkylated product 5 (1.23 g, 3.96 mmol, 93%) wasobtained as pale yellow oil: 1H-NMR (CDCl3, 400 MHz) δ:2.20 (2H, quint, J=6.3 Hz), 3.63 (2H, t, J=6.3 Hz), 4.02 (2H,t, J=6.3 Hz), 6.84 (1H, d, J=1.8 Hz), 6.88-6.91 (2H, m), 6.94(1H, td, J=7.5 and 1.2 Hz), 7.02 (1H, d, J=8.0 Hz), 7.12-7.19(2H, m); 13C-NMR (CDCl3, 75 MHz) δ: 29.4, 42.2, 44.0, 115.8,115.9, 122.5, 123.4, 124.1, 125.3, 127.5, 127.6, 128.0, 133.3,144.2, 146.3; HR-MS ESI-TOF m/z: Calcd for C15H13Cl2NS(M+) 309.0146. Found 309.0166; IR (neat) 749, 803, 854, 914,1039, 1098, 1127, 1247, 1281, 1408, 1456, 1567, 1591, 2864,2928, 2957, 3060 cm-1.

References:

Kohiki, Taiki;Nishikawa, Yusuke;Inokuma, Tsubasa;Shigenaga, Akira;Otaka, Akira [Chemical and Pharmaceutical Bulletin,2017,vol. 85,# 12,p. 1161 - 1166]

6940-76-7 Synthesis