13745-86-3

Basic information

• Product Name: 11-Chloro-dibenzo[b,f][1,4]thiazepine
• Synonyms: DIBENZO[B,F][1,4]THIAZEPINE, 11-CHLORO-;11-CHLORODIBENZO[B,F]-[1,4]THIAZEPINE;11-cholro-dibanzo(b,f)[1,4]thiazepine;11-Piperazin-1-Yl-Dibenzo-B,F-1,4ThiazepinDihydrochloride;11-Chloro-dibenzo[b,f][1,4]thiazepine Discontinued (unstable);11-Chloro-dibenzo[b,f][1,4]thiazepine (unstable);Quetiapine DBTC IMpurity;Quetiapine IMpurity F (11-Chlorodibenzo[b,f][1,4]thiazepine)
• CAS NO: 13745-86-3
• Molecular Formula: C₁₃H₈ClNS
• Molecular Weight: 245.73
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 13745-86-3.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 384.595 °C at 760 mmHg
• Flash Point: 186.397 °C
• Appearance: Pale-Yellow Solid
• Density: 1.329 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 11-Chloro-dibenzo[b,f][1,4]thiazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Chloro-dibenzo[b,f][1,4]thiazepine(13745-86-3)
• EPA Substance Registry System: 11-Chloro-dibenzo[b,f][1,4]thiazepine(13745-86-3)

Safety Data

• Hazardous Substances Data: 13745-86-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale-Yellow Solid

Uses

A metabolite of Quetiapine

InChI:InChI=1/C13H8ClNS/c14-13-9-5-1-3-7-11(9)16-12-8-4-2-6-10(12)15-13/h1-8H

Synthetic route

dibenzo[b,f][1,4]thiazepin-11-one (3159-07-7) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
With trichlorophosphate In toluene at 100℃; for 12h; Inert atmosphere;	99%
With N,N-dimethyl-aniline; trichlorophosphate at 106℃; for 6h; Heating / reflux;	97%
With N,N-dimethyl-aniline; trichlorophosphate at 106℃; for 6h; Heating / reflux;	97%

2-((2-aminophenyl)thio)benzoic acid (54920-98-8) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
With trichlorophosphate for 5 - 6h; Product distribution / selectivity; Heating / reflux;
With triethylamine; trichlorophosphate In toluene for 5 - 6h; Product distribution / selectivity; Heating / reflux;
With trichlorophosphate In toluene for 5 - 6h; Product distribution / selectivity; Heating / reflux;

dibenzo[b,f][1,4]thiazepin-11-one (3159-07-7) + dibenzo[b,f][1,4]thiazepine(10H)one → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
With phosphorus pentachloride; nitrogen In dichloromethane
With phosphorus pentachloride; nitrogen In dichloromethane; toluene

phenyl [2-(phenylsulphanyl)phenyl]carbamate (111974-73-3) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / Heating 2: N,N-dimethyl-aniline; trichlorophosphate / 105 °C View Scheme
Multi-step reaction with 2 steps 1: PPA / 100 °C 2: trichlorophosphate / N,N-dimethyl-aniline; dichloromethane View Scheme
Multi-step reaction with 2 steps 1: polyphosphoric acid / 8 h / 100 - 105 °C 2: N,N-dimethyl-aniline; trichlorophosphate / toluene View Scheme
Multi-step reaction with 2 steps 1: methanesulfonic acid; phosphorus pentoxide / 2.5 h / 80 - 110 °C 2: trichlorophosphate; N,N-dimethyl-aniline / 3 h / 120 °C View Scheme

2-nitrophenyl phenyl sulfide (4171-83-9) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen / methanol / 4137.29 Torr 2: sodium carbonate 3: polyphosphoric acid / Heating 4: N,N-dimethyl-aniline; trichlorophosphate / 105 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogen / methanol / 4137.29 Torr 2: sodium carbonate / tetrahydrofuran; water 3: PPA / 100 °C 4: trichlorophosphate / N,N-dimethyl-aniline; dichloromethane View Scheme
Multi-step reaction with 4 steps 1: iron; ammonium chloride / water 2: sodium carbonate / toluene 3: polyphosphoric acid / 8 h / 100 - 105 °C 4: N,N-dimethyl-aniline; trichlorophosphate / toluene View Scheme

2-phenylsulfanyl-aniline (1134-94-7) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate 2: polyphosphoric acid / Heating 3: N,N-dimethyl-aniline; trichlorophosphate / 105 °C View Scheme
Multi-step reaction with 3 steps 1: sodium carbonate / tetrahydrofuran; water 2: PPA / 100 °C 3: trichlorophosphate / N,N-dimethyl-aniline; dichloromethane View Scheme
Multi-step reaction with 3 steps 1: sodium carbonate / toluene 2: polyphosphoric acid / 8 h / 100 - 105 °C 3: N,N-dimethyl-aniline; trichlorophosphate / toluene View Scheme
Multi-step reaction with 3 steps 1.1: toluene / 0.08 h / 4 °C 1.2: 1.5 h / 4 °C 2.1: methanesulfonic acid; phosphorus pentoxide / 2.5 h / 80 - 110 °C 3.1: trichlorophosphate; N,N-dimethyl-aniline / 3 h / 120 °C View Scheme

thiophenol (108-98-5) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / dimethyl sulfoxide / 80 °C 2: hydrogen / methanol / 4137.29 Torr 3: sodium carbonate / tetrahydrofuran; water 4: PPA / 100 °C 5: trichlorophosphate / N,N-dimethyl-aniline; dichloromethane View Scheme
Multi-step reaction with 5 steps 1: copper; sodium hydroxide / tetralin / 6 h / 130 °C 2: sulfuric acid / toluene / 1 h / 0 - 80 °C 3: hydroxylamine hydrochloride / ethanol / 3 h / Reflux 4: toluene-4-sulfonic acid / toluene / Reflux 5: trichlorophosphate / 4 h / Reflux View Scheme
Multi-step reaction with 5 steps 1: sodium hydroxide / methanol 2: iron; ammonium chloride / water 3: sodium carbonate / toluene 4: polyphosphoric acid / 8 h / 100 - 105 °C 5: N,N-dimethyl-aniline; trichlorophosphate / toluene View Scheme

2-Chloronitrobenzene (88-73-3) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / dimethyl sulfoxide / 80 °C 2: hydrogen / methanol / 4137.29 Torr 3: sodium carbonate / tetrahydrofuran; water 4: PPA / 100 °C 5: trichlorophosphate / N,N-dimethyl-aniline; dichloromethane View Scheme
Multi-step reaction with 5 steps 1: sodium hydroxide / methanol 2: iron; ammonium chloride / water 3: sodium carbonate / toluene 4: polyphosphoric acid / 8 h / 100 - 105 °C 5: N,N-dimethyl-aniline; trichlorophosphate / toluene View Scheme

Thiosalicylic acid (147-93-3) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide / water; isopropyl alcohol 2: ethyl acetate 3: triethylamine; benzotriazol-1-ol / dichloromethane 4: trichlorophosphate View Scheme
Multi-step reaction with 4 steps 1: potassium hydroxide / water; isopropyl alcohol / 20 °C 2: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 12 h / 20 °C 4: trichlorophosphate / 2 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium hydroxide / isopropyl alcohol; water / 20 °C 2: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 12 h / 20 °C 4: trichlorophosphate / 2 h / Reflux View Scheme

ortho-nitrofluorobenzene (1493-27-2) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide / water; isopropyl alcohol 2: ethyl acetate 3: triethylamine; benzotriazol-1-ol / dichloromethane 4: trichlorophosphate View Scheme
Multi-step reaction with 4 steps 1: potassium hydroxide / water; isopropyl alcohol / 20 °C 2: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 12 h / 20 °C 4: trichlorophosphate / 2 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium hydroxide / isopropyl alcohol; water / 20 °C 2: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 12 h / 20 °C 4: trichlorophosphate / 2 h / Reflux View Scheme

2‑(2‑nitrophenylsulfanyl)benzoic acid (19806-43-0) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethyl acetate 2: triethylamine; benzotriazol-1-ol / dichloromethane 3: trichlorophosphate View Scheme
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 12 h / 20 °C 3: trichlorophosphate / 2 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 2: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 12 h / 20 °C 3: trichlorophosphate / 2 h / Reflux View Scheme

2-(phenylthio)benzoic acid (1527-12-4) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / toluene / 1 h / 0 - 80 °C 2: hydroxylamine hydrochloride / ethanol / 3 h / Reflux 3: toluene-4-sulfonic acid / toluene / Reflux 4: trichlorophosphate / 4 h / Reflux View Scheme

thio-xanthene-9-one (492-22-8) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / ethanol / 3 h / Reflux 2: toluene-4-sulfonic acid / toluene / Reflux 3: trichlorophosphate / 4 h / Reflux View Scheme

9H-thioxanthen-9-one oxime (20169-45-3) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / Reflux 2: trichlorophosphate / 4 h / Reflux View Scheme

ortho-chlorobenzoic acid (118-91-2) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: copper; sodium hydroxide / tetralin / 6 h / 130 °C 2: sulfuric acid / toluene / 1 h / 0 - 80 °C 3: hydroxylamine hydrochloride / ethanol / 3 h / Reflux 4: toluene-4-sulfonic acid / toluene / Reflux 5: trichlorophosphate / 4 h / Reflux View Scheme

2-amino-benzenethiol (137-07-5) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate; iron; copper / N,N-dimethyl-formamide / 3 h / 120 °C 2.1: toluene / 0.08 h / 4 °C 2.2: 1.5 h / 4 °C 3.1: methanesulfonic acid; phosphorus pentoxide / 2.5 h / 80 - 110 °C 4.1: trichlorophosphate; N,N-dimethyl-aniline / 3 h / 120 °C View Scheme

iodobenzene (591-50-4) → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate; iron; copper / N,N-dimethyl-formamide / 3 h / 120 °C 2.1: toluene / 0.08 h / 4 °C 2.2: 1.5 h / 4 °C 3.1: methanesulfonic acid; phosphorus pentoxide / 2.5 h / 80 - 110 °C 4.1: trichlorophosphate; N,N-dimethyl-aniline / 3 h / 120 °C View Scheme

dibenzo[b,f][1,4]thiazepin-11-ol → 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3)

Conditions	Yield
With trichlorophosphate at 70℃; for 3h;

1-[2-(2-hydroxyethoxy)ethyl]piperazine (13349-82-1) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → Quetiapine (111974-69-7)

Conditions	Yield
In toluene at 105 - 107℃;	99%
In toluene at 110 - 120℃; for 8h; Product distribution / selectivity;	98%
In toluene Reflux;	92%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + (2-(piperazin-1-yl)ethoxy)methanol → Quetiapine (111974-69-7)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 80℃; for 8h; Reagent/catalyst; Inert atmosphere;	99%

4-ethylpiperazine (5308-25-8) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-[4-ethyl-1-piperazinyl]dibenzo[b,f][1,4]thiazepine (1011758-03-4)

Conditions	Yield
With tetrabutylammomium bromide; sodium carbonate In toluene for 5h;	96%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + butyl magnesium bromide (693-04-9) → 11-butyl-dibenzo[b,f][1,4]thiazepine

Conditions	Yield
iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at -78 - 20℃; for 0.0833333h; Product distribution / selectivity;	93%
iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 0.0833333h; Product distribution / selectivity;	93%

pyrrolidine (123-75-1) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-(pyrrolidin-1-yl)dibenzo[b,f][1,4]thiazepine (1345730-54-2)

Conditions	Yield
With triethylamine In toluene at 100℃; for 6h;	92%

1H-imidazole (288-32-4) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-(imidazol-1-yl)dibenzo[b,f][1,4]thiazepine (1345730-51-9)

Conditions	Yield
With triethylamine In toluene at 100℃; for 7h;	92%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + 4-Aminoacetophenone (99-92-3) → 1-(4-(dibenzo[b,f][1,4]thiazepin-11-ylamino)phenyl)ethanone

Conditions	Yield
With pyridine for 4h; Heating;	91%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + cyclohexylmagnesiumchloride (931-51-1) → 11-cyclohexyl-dibenzo[b,f][1,4]thiazepine

Conditions	Yield
iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at -78 - 20℃; for 0.0833333h; Product distribution / selectivity;	89%
iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 0.0833333h; Product distribution / selectivity;	89%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + 1,2,4-Triazole (288-88-0) → 11-(1,2,4-triazol-1-yl)dibenzo[b,f][1,4]thiazepine (1345730-55-3)

Conditions	Yield
With triethylamine In toluene at 100℃; for 6h;	89%

piperazine (110-85-0) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-(1-piperazinyl)dibenzo[b,f][1,4]thiazepine (5747-48-8)

Conditions	Yield
With hydrogenchloride In ethanol; toluene	88%
With hydrogenchloride In ethanol; toluene	88%
With hydrogenchloride In ethanol; toluene	88%

piperazine (110-85-0) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-[4-(2-hydroxyethyl)-1-piperazinyl]dibenzo[b,f][1,4]thiazepine (945668-94-0)

Conditions	Yield
With potassium carbonate; potassium iodide In 5,5-dimethyl-1,3-cyclohexadiene at 105 - 115℃; for 5h; Reagent/catalyst;	88%
In toluene for 4h; Heating;

piperazine (110-85-0) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride (753475-15-9)

Conditions	Yield
With hydrogenchloride In isopropyl alcohol; toluene	88%

2-methylimidazole (693-98-1) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-(2-methylimidazol-1-yl)dibenzo[b,f][1,4]thiazepine (1345730-52-0)

Conditions	Yield
With triethylamine In toluene at 100℃; for 8h;	88%

piperazine (110-85-0) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → N-Dealkyl Quetiapine dihydrochloride

Conditions	Yield
With IPA-HCl In toluene	87%
In toluene
In dimethyl sulfoxide; toluene at 25 - 30℃; for 3h; Product distribution / selectivity; Industry scale; Inert atmosphere;

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + (1,3-dioxan-2-yl)ethylmagnesium bromide → 11-(2-[1,3]dioxane-2-yl-ethyl)-dibenzo[b,f][1,4]thiazepine

Conditions	Yield
iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at -78 - 20℃; for 0.0833333h; Product distribution / selectivity;	86%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + 1,3-dioxane-2-yl-ethyl magnesium chloride → 11-(2-[1,3]dioxane-2-yl-ethyl)-dibenzo[b,f][1,4]thiazepine

Conditions	Yield
iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 0.0833333h; Product distribution / selectivity;	86%

(2-hydroxyethyl)(methyl)amine (109-83-1) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → C16H16N2OS

Conditions	Yield
With triethylamine In toluene at 60 - 65℃; for 8h;	83%

4-methyl-1H-imidazole (822-36-6) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-(4-methylimidazol-1-yl)dibenzo[b,f][1,4]thiazepine (1345730-53-1)

Conditions	Yield
With triethylamine In toluene at 100℃; for 8h;	80%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + Cyclopropylamine (765-30-0) → 11-(cyclopropylamino)dibenzo[b,f][1,4]thiazepine hydrochloride

Conditions	Yield
Stage #1: 11-chloro-dibenzo[b,f][1,4]thiazepine; Cyclopropylamine With triethylamine In water; toluene at 60 - 70℃; for 6h; Stage #2: With hydrogenchloride In hexane	79%

piperazine (110-85-0) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine (1159882-47-9)

Conditions	Yield
In o-xylene at 20 - 142℃; for 40h; Heating / reflux;	78%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + benzylamine (100-46-9) → 11-(benzylamino)dibenzo[b,f][1,4]thiazepine (1345730-60-0)

Conditions	Yield
With triethylamine at 60 - 65℃; for 4h;	76%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + (R)-2-benzylpiperazine (131288-11-4) → 11-(3-(R)-benzylpiperazin-1-yl)dibenzo[b,f][1,4]thiazepine

Conditions	Yield
In toluene for 19h; Heating / reflux;	74%

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → (E)-tert-butyl 4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazine-1-carboxylate (1217310-64-9)

Conditions	Yield
In o-xylene at 130℃; for 7h;	62%

1-(2-hydroxyethyl)piperazine (103-76-4) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → O-Dealkyl Quetiapine (329216-67-3)

Conditions	Yield
In xylene at 170℃; for 12 - 18h;	53%
In xylene Heating;
In 1-methyl-pyrrolidin-2-one; toluene for 6 - 8h; Heating / reflux;

11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + 7-(benzyloxy)-12-(10,11-difluoro-7,12-dihydrobenzo[e]naphtho[1,2-b]thiepin-7-yl)-3,4,12,12a-tetrahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazine-6,8-dione → 7-(benzyloxy)-12-(dibenzo[b,f][1,4]thiazepin-11-yl)-3,4,12,12a-tetrahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazine-6,8-dione

Conditions	Yield
Stage #1: 7-(benzyloxy)-12-(10,11-difluoro-7,12-dihydrobenzo[e]naphtho[1,2-b]thiepin-7-yl)-3,4,12,12a-tetrahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazine-6,8-dione With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 11-chloro-dibenzo[b,f][1,4]thiazepine In dimethyl sulfoxide at 80℃; for 0.5h; Inert atmosphere;	46%

1-[2-(2-hydroxyethoxy)ethyl]piperazine (13349-82-1) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) + (2E)-but-2-enedioic acid (110-17-8) → quetiapine hemi-fumarate

Conditions	Yield
Stage #1: 1-[2-(2-hydroxyethoxy)ethyl]piperazine; 11-chloro-dibenzo[b,f][1,4]thiazepine With triethylamine In toluene at 95℃; for 60h; Stage #2: (2E)-but-2-enedioic acid In ethanol at 25℃; for 0.5h; Product distribution / selectivity;	40%

α-picoline (109-06-8) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → C19H14N2S

Conditions	Yield
Stage #1: α-picoline With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 11-chloro-dibenzo[b,f][1,4]thiazepine In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	28%

piperidine (110-89-4) + 11-chloro-dibenzo[b,f][1,4]thiazepine (13745-86-3) → 11-piperidin-1-yl-dibenzo[b,f][1,4]thiazepine (5814-72-2)

Conditions	Yield
In xylene for 5h; Heating;

Upstream product

• 3159-07-7 dibenzo[b,f][1,4]thiazepin-11-one 
• 111974-73-3 phenyl [2-(phenylsulphanyl)phenyl]carbamate 
• 4171-83-9 2-nitrophenyl phenyl sulfide 
• 1134-94-7 2-phenylsulfanyl-aniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 20169-45-3 9H-thioxanthen-9-one oxime 
• 492-22-8 thio-xanthene-9-one 
• 1527-12-4 2-(phenylthio)benzoic acid 
• 19806-43-0 2?(2?nitrophenylsulfanyl)benzoic acid 
• 1493-27-2 ortho-nitrofluorobenzene 
• 147-93-3 Thiosalicylic acid 
• 88-73-3 2-Chloronitrobenzene 
• 108-98-5 thiophenol 
• 54920-98-8 2-((2-aminophenyl)thio)benzoic acid 

Downstream Products

• 1977-09-9 11-(N-Methyl-piperazino)-dibenzo-1,4-thiazepin 
• 5786-26-5 11-aminodibenzo<1,4>thiazepine 
• 5747-48-8 11-(1-piperazinyl)dibenzo[b,f][1,4]thiazepine 
• 945668-94-0 11-[4-(2-hydroxyethyl)-1-piperazinyl]dibenzo[b,f][1,4]thiazepine 
• 111974-74-4 N-Dealkyl Quetiapine dihydrochloride 
• 753475-15-9 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride 
• 111974-72-2 quetiapine fumarate 
• 1345730-60-0 11-(benzylamino)dibenzo[b,f][1,4]thiazepine 
• 1421365-58-3 C₂₄H₁₆ClN₃O₃S 
• 1011758-03-4 11-[4-ethyl-1-piperazinyl]dibenzo[b,f][1,4]thiazepine 
• 111974-69-7 Quetiapine 

Relevant articles and documents

Synthesis of diverse fused tetracyclic thiazepine-chalcone derivatives by claisen-schmidt condensation reaction and their antimicrobial activity

To develop antimicrobial agent, a series of thiazepine-chalcones was synthesized by Claisen-Schmidt condensation between the couplings of aryl ketone in three steps protocol and different aromatic aldehydes under strong base catalyst at room temperature. The characterization of final products were carried out by IR, 1H & 13C NMR and elemental analysis. The synthesized compounds were also evaluated for their antibacterial and antifungal activities using specific Gram positive and Gram-negative bacterial strains using cup plate method.

INFLUENZA VIRUS REPLICATION INHIBITOR AND USE THEREOF

Disclosed are a compound as shown in formula (I) as an influenza virus replication inhibitor and a preparation method therefor, a pharmaceutical composition comprising the compound and the use of the compound and pharmaceutical composition thereof in the treatment of influenza.

Antibodies to quetiapine haptens and use thereof

Disclosed is an antibody which binds to quetiapine, which can be used to detect quetiapine in a sample such as in a competitive immunoassay method. The antibody can be used in a lateral flow assay device for point-of-care detection of quetiapine, including multiplex detection of aripiprazole, olanzapine, quetiapine, and risperidone in a single lateral flow assay device.