2-Chlorophenothiazine synthesis
- Product Name:2-Chlorophenothiazine
- CAS Number:92-39-7
- Molecular formula:C12H8ClNS
- Molecular Weight:233.72
Yield:92-39-7 87%
Reaction Conditions:
Stage #1:1-Bromo-2-iodobenzene;4-chloro-2-aminobenzenethiol with ferric citrate in N,N-dimethyl-formamide at 110;Green chemistry;
Stage #2: with potassium carbonate in N,N-dimethyl-formamide at 110;Green chemistry;regioselective reaction;
Steps:
Procedure for synthesis of compound (3 and 4)
General procedure: 2-aminobenzenethiol (10 g, 80mmol), 3, 4-difluorobenzonitrile (11.12, 80mmol) and ferric citrate (19.59g, 80mmol) were added in DMF (50.00 mL) at 25-30 0C. The reaction mixture was heated to 110°C. Reaction mixture was monitored for the synthesis of compound 3 by TLC. (2ml of reaction mixture was withdrawn and separated in ethylacetate and water. Ethyl acetate solution concentrated and crystallised in isopropyl ether to give compound 3 for characterization). After completion of reaction by TLC, powdered potassium carbonate (16.58 g, 120mmol) was added to the solution and stirred for 1 hr. The mixture was heated to 110°C till completion by TLC. After completion of reaction, the mass was cooled to 25-30 °C. Ethyl acetate (150 mL) and DM water (150 mL) were added. Layers separated. Organic layer washed with water (150 mL), dried over sodium sulfate and concentrated. Isopropyl ether (IPE; 150 mL) was added to the slurry, filtered, washed with IPE. Dried under vacuum at 50 °C (16.84g, 94%).
References:
Das, Tonmoy Chitta;Quadri, Syed Aziz Imam;Farooqui, Mazahar [Letters in Organic Chemistry,2019,vol. 16,# 1,p. 16 - 24] Location in patent:supporting information
