ChemicalBook CAS DataBase List 7-CHLORO-2H-1,4-BENZOTHIAZIN-3(4H)-ONE

7-CHLORO-2H-1,4-BENZOTHIAZIN-3(4H)-ONE synthesis

13synthesis methods

Product Name:7-CHLORO-2H-1,4-BENZOTHIAZIN-3(4H)-ONE
CAS Number:5333-05-1
Molecular formula:C8H6ClNOS
Molecular Weight:199.66

23474-98-8
70 suppliers
$75.00/100 mg

96-32-2
333 suppliers
$15.00/5g

5333-05-1
38 suppliers
$26.60/1g

Yield:-

Reaction Conditions:

Stage #1:2-amino-5-chlorobenzenethiol with sodium ethanolate in dimethyl sulfoxide at 20; for 1 h;
Stage #2:bromoacetic acid methyl ester in dimethyl sulfoxide at 65; for 1 h;

Steps:

Intermediate 41 : 7-chloro-2H-1 ,4-benzothiazin-3(4H)-oneTo a solution of 2-amino-5-chlorobenzenethiol (Intermediate 40, 6 g, 33.8 mmol) in Dimethyl Sulfoxide (DMSO) (150 mL) at room temperature was added sodium ethoxide (2.53 g, 37.2 mmol). After the mixture was stirred for 1 hour, methyl bromoacetate (3.43 mL, 37.2 mmol) was added. The mixture was then heated at 65 °C for 3 hours. Then 350 ml of cold water was added. The resulting precipitate was filtered and was dried in a vacuum oven at 40 °C to give the title compound (3.5 g). the organic substances from the filtrate were extracted with diethyl ether (800 ml in total, several times). The organic layers were washed with the mixture of 1 N HCI (3 x 300 ml). The organic layer was dried over IS^SC^ and the solvent evaporated to give the title compound (3 g); m/z (ES): 199.98 [M+H]⁺; ¹H NMR (500 MHz,CHLOROFORM-d) Bppm 3.43 (s, 2 H) 6.79 (d, J=8.54 Hz, 1 H) 7.14 (dd, J=8.47, 2.21 Hz, 1 H) 7.32 (d, J=2.14 Hz, 1 H) 8.49 (br. s., 1 H).

References:

GLAXO GROUP LIMITED;BERTANI, Barbara;CREMONESI, Susanna;GARZYA, Vincenzo;MICHELI, Fabrizio;RUPCIC, Renata;SABBATINI, Fabio Maria WO2011/151361, 2011, A1 Location in patent:Page/Page column 44

23474-98-8
70 suppliers
$75.00/100 mg

105-36-2 Synthesis