Heptane → 4-(3-Chloropropyl)-4H-benzo[1,4]thiazin-3-one

2H-1,4-benzothiazine-3(4H)-one (1.0 g, 6.05 mmol) and Cs2CO3 (2.96 g, 9.08 mmol) were dissolved in dry acetonitrile (20 mL) under nitrogen atmosphere and stirred at rt for 30 min. 3-chloro-1-iodopropane (1.37 g, 6.66 mmol) dissolved in acetonitrile (4 mL) was added via a syringe. The reaction mixture was stirred at rt for 18 hours and concentrated in vacuo. Water (150 mL) was added and the reaction mixture was extracted with ethyl acetate (3×150 mL). The combined organic phases were dried (MgSO4) and concentrated in vacou to give 1.45 g of crude. The crude product was subjected to CC[eluent:Heptane:EtOAC(4:1)] to give the pure title compound as a slightly yellow oil. Yield 1.37 g, 90.2%. Rf=0.24 [Heptane:EtOAC(4:1)], 1H NMR (CDCl3): δ 2.14 (m, 2H), 3.38 (s, 2H), 3.36 (t, 2H), 4.17 (t, 2H), 7.03 (t, 1H), 7.18 (d, 1H), 7.26 (t, 1H), 7.37 (d, 1H). 13C NMR (CDCl3): δ 30.61, 31.81, 42.48, 42.66, 117.87, 123.78, 124.29, 127.52, 127.52, 128.78, 139.40, 165.51

1. additionwas added via a syringe
2. stirringThe reaction mixture was stirred at rt for 18 hours
3. concentrationconcentrated in vacuo
4. additionWater (150 mL) was added
5. extractionthe reaction mixture was extracted with ethyl acetate (3×150 mL)
6. dry with materialThe combined organic phases were dried (MgSO4)
7. concentrationconcentrated in vacou
8. customto give 1.45 g of crude

ORD record

ord-38656ab4d7a94e668a5bd2e5045d9eb3

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680115B2