261-96-1

Basic information

• Product Name: 10H-pyrido(3,2-b)(1,4)benzothiazine
• Synonyms: 10H-pyrido(3,2-b)(1,4)benzothiazine;PYRIDO[3,2-B][1,4]BENZOTHIAZINE;1-Azaphenothiazine;1H-Pyrido[3,2-b][1,4]benzothiazine;NSC 277720;10H-Benzo[b]pyrido[2,3-e][1,4]thiazine;10H-benzo[e]pyrido[3,2-b][1,4]thiazine
• CAS NO: 261-96-1
• Molecular Formula: C₁₁H₈N₂S
• Molecular Weight: 200.25962
• EINECS: 205-973-7
• Mol File: 261-96-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 110.0 to 114.0 °C
• Boiling Point: 370°C(lit.)
• Flash Point: 197 °C
• Appearance: /
• Density: 1.293
• Vapor Pressure: 1.13E-06mmHg at 25°C
• Refractive Index: 1.684
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane (Slightly), DMSO (Slightly)
• PKA: 4.24±0.20(Predicted)
• CAS DataBase Reference: 10H-pyrido(3,2-b)(1,4)benzothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 10H-pyrido(3,2-b)(1,4)benzothiazine(261-96-1)
• EPA Substance Registry System: 10H-pyrido(3,2-b)(1,4)benzothiazine(261-96-1)

Safety Data

• Hazardous Substances Data: 261-96-1(Hazardous Substances Data)

Usage

Uses

10H-Pyrido[3,2-b][1,4]benzothiazine has potential anti-cancer ability as seen through studies.

InChI:InChI=1/C11H8N2S/c1-2-5-9-8(4-1)13-11-10(14-9)6-3-7-12-11/h1-7H,(H,12,13)

Synthetic route

10-acetyl-10H-benzo[b]pyrido[2,3-e][1,4]thiazine (95873-97-5) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
With hydrogenchloride In ethanol; water at 70℃; for 12h; Inert atmosphere;	86%
With hydrogenchloride

N-(2-Mercaptophenyl)-2-pyridinamin → 2-Methylbenzothiazole (120-75-2) + 1-azaphenothiazine (261-96-1)

Conditions	Yield
With iodine In diphenylether; biphenyl at 200 - 205℃; for 2.5h;	A n/a B 45%

2,3-dibromopyridine (13534-89-9) + 2-amino-benzthiazole (136-95-8) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In dimethyl sulfoxide at 170℃; for 24h; Inert atmosphere;	39%

2,3-dibromopyridine (13534-89-9) + N-(2-mercaptophenyl) acetamide (1444-47-9) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
With 1,10-Phenanthroline; potassium tert-butylate In N,N-dimethyl-formamide at 135℃;	25%

2-(phenylamino)pyridine (6631-37-4) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
With iodine; sulfur at 160 - 180℃;
With iodine; sulfur at 250 - 335℃;
With sulfur
With iodine; sulfur In water at 190℃; for 0.333333h; microwave irradiation;

iodine (7553-56-2) + 2-(phenylamino)pyridine (6631-37-4) + sulfur → 1-azaphenothiazine (261-96-1)

Conditions	Yield
at 160 - 180℃;

2-aminopyridine (504-29-0) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: K3PO4; X-phos / Pd2dba3 / toluene / 20 h / Heating 2: sulfur; I2 / H2O / 0.33 h / 190 °C / microwave irradiation View Scheme

bromobenzene (108-86-1) + potassium hexacyanoferrate (II) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: K3PO4; X-phos / Pd2dba3 / toluene / 20 h / Heating 2: sulfur; I2 / H2O / 0.33 h / 190 °C / microwave irradiation View Scheme

2-<(2-aminophenyl)thio>-3-nitropyridine (92316-06-8) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
Multi-step reaction with 3 steps 2: aq.-ethanolic KOH 3: aq.-ethanolic HCl View Scheme
Multi-step reaction with 2 steps 1: 20 °C 2: potassium hydroxide / acetone / Reflux View Scheme

2-acetylaminophenyl-(3-nitro-2-pyridyl)sulfide (91902-18-0) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH 2: aq.-ethanolic HCl View Scheme
With potassium hydroxide In acetone Smiles Aromatic Rearrangement; Reflux;

2-amino-benzenethiol (137-07-5) → 1-azaphenothiazine (261-96-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol; ethanol; KOH-solution / anschliessenden Erwaermen mit 2-Chlor-3-nitro-pyridin 3: aq.-ethanolic KOH 4: aq.-ethanolic HCl View Scheme

chloropropionic acid (107-94-8) + 1-azaphenothiazine (261-96-1) → 10-(3-chloropropyl)-10H-benzo[b]pyrido[2,3-e][1,4]thiazine hydrochloride

Conditions	Yield
Stage #1: chloropropionic acid With sodium tetrahydroborate In toluene at 0 - 5℃; Stage #2: 1-azaphenothiazine With sodium tetrahydroborate In toluene at 25 - 75℃; for 6h; Stage #3: With hydrogenchloride In water; isopropyl alcohol	98%

1-azaphenothiazine (261-96-1) + 3-dimethylaminopropionic acid (6300-04-5) → Prothipendyl hydrochloride (1225-65-6)

Conditions	Yield
Stage #1: 3-dimethylaminopropionic acid With sodium tetrahydroborate In toluene at 0 - 5℃; Stage #2: 1-azaphenothiazine With sodium tetrahydroborate In toluene at 25 - 75℃; for 6h; Stage #3: With hydrogenchloride In water; isopropyl alcohol	96%

1-azaphenothiazine (261-96-1) + 2-(4'-bromobiphenyl-4-yl)-4,6-diphenylpyrimidine → C39H26N4S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	80%

2-chloropyrazin (14508-49-7) + 1-azaphenothiazine (261-96-1) → 10-Pyrazin-2-yl-10H-benzo[b]pyrido[2,3-e][1,4]thiazine (89480-07-9)

Conditions	Yield
With copper; potassium carbonate; potassium iodide at 230 - 250℃; for 96h;	77%

1-azaphenothiazine (261-96-1) + 2-(4’-bromo-[1,1‘-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine → C38H25N5S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	75%

2-Chloroquinoline (612-62-4) + 1-azaphenothiazine (261-96-1) → 10-Quinolin-2-yl-10H-benzo[b]pyrido[2,3-e][1,4]thiazine (89480-08-0)

Conditions	Yield
With copper; potassium carbonate; potassium iodide at 230 - 250℃; for 96h;	73%

1-azaphenothiazine (261-96-1) + tert-butyl 4-(4-bromophenoxy)piperidine-1-carboxylate (308386-38-1) → C27H29N3O3S (1206478-95-6)

Conditions	Yield
With potassium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 140℃; for 18h; sealed pressure tube;	72%

1 ,6-dibromohexane (629-03-8) + 1-azaphenothiazine (261-96-1) → 1,6-bis(10H-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl)hexane (1421278-69-4)

Conditions	Yield
Stage #1: 1-azaphenothiazine With sodium hydride In N,N-dimethyl-formamide at -5℃; Inert atmosphere; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at -5 - 20℃; Inert atmosphere;	71%

1,4-dibromo-butane (110-52-1) + 1-azaphenothiazine (261-96-1) → 1,4-bis(10H-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl)butane (1421278-73-0)

Conditions	Yield
Stage #1: 1-azaphenothiazine With sodium hydride In N,N-dimethyl-formamide at -5℃; Inert atmosphere; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at -5 - 20℃; Inert atmosphere;	70%

1-azaphenothiazine (261-96-1) + (E)-1,4-dibromobutene (821-06-7) → 1,4-bis(10H-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl)but-2E-ene (1421278-77-4)

Conditions	Yield
Stage #1: 1-azaphenothiazine With sodium hydride In N,N-dimethyl-formamide at -5℃; Inert atmosphere; Stage #2: (E)-1,4-dibromobutene In N,N-dimethyl-formamide at -5 - 20℃; Inert atmosphere;	68%

1-azaphenothiazine (261-96-1) + 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine → C38H25N5S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	68%

1-azaphenothiazine (261-96-1) + 2-(3′-chloro-[1,1′-biphenyl]-3-yl)-4,6-diphenylpyrimidine → C39H26N4S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	67%

1-azaphenothiazine (261-96-1) + Methyl 4-(bromomethyl)benzoate (2417-72-3) → methyl 4-[(10H-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl)methyl]benzoate

Conditions	Yield
Stage #1: 1-azaphenothiazine With lithium hexamethyldisilazane In N,N-dimethyl-formamide; toluene at 0℃; for 0.25h; Inert atmosphere; Stage #2: Methyl 4-(bromomethyl)benzoate In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 24h; Inert atmosphere;	67%

2-chloropyridine (109-09-1) + 1-azaphenothiazine (261-96-1) → 10-(2'-pyridyl)pyrido<3,2-b><1,4>benzothiazine (89480-06-8)

Conditions	Yield
With copper; potassium carbonate; potassium iodide at 230 - 250℃; for 96h;	65%

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) + 1-azaphenothiazine (261-96-1) → 10-(6-(tetrahydro-2H-pyran-2-yloxy)hexyl)-10H-benzo[b]pyrido[2,3-e][1,4]thiazine

Conditions	Yield
Stage #1: 1-azaphenothiazine With sodium hydride In N,N-dimethyl-formamide at -5 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran In N,N-dimethyl-formamide at 20℃; for 14h; Inert atmosphere;	61%

1-azaphenothiazine (261-96-1) + 3-fluoro-4-methoxybenzyl bromide (331-61-3) → 10-(3-fluoro-4-methoxybenzyl)-10H-pyrido[3,2-b][1,4]benzothiazine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;	61%

1 ,6-dibromohexane (629-03-8) + 1-azaphenothiazine (261-96-1) → 10-(6-bromohexyl)-10H-benzo[b]pyrido[2,3-e][1,4]thiazine

Conditions	Yield
Stage #1: 1-azaphenothiazine With potassium hydroxide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	55%

dimethylsulphoxide (DMSO) + 1-azaphenothiazine (261-96-1) + 2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7) → 3-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl-propylamine (89929-26-0)

Conditions	Yield
With hydrazine hydrate In hydrogenchloride; ethanol; dimethyl sulfoxide	8.3%

phosgene (75-44-5) + 1-azaphenothiazine (261-96-1) → 1-azaphenothiazine-10-carbonyl chloride (94231-78-4)

Conditions	Yield
With hydrogenchloride; chlorobenzene at 170℃;
With hydrogenchloride In chlorobenzene at 170℃;

3-Chloropropionitrile (542-76-7) + 1-azaphenothiazine (261-96-1) → 3-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl-propionitrile (5622-88-8)

Conditions	Yield
With sodium amide; xylene

1-azaphenothiazine (261-96-1) + acetic anhydride (108-24-7) → 10-acetyl-10H-benzo[b]pyrido[2,3-e][1,4]thiazine (95873-97-5)

Conditions	Yield
With sodium acetate

1-azaphenothiazine (261-96-1) + dimethyl amine (124-40-3) + 1-Bromo-2-chloroethane (107-04-0) → (2-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl-ethyl)-dimethyl-amine (67465-69-4)

Conditions	Yield
With sodium amide; toluene aufeinanderfolgendes Erhitzen;

1-azaphenothiazine (261-96-1) + 1-Bromo-2-chloroethane (107-04-0) + diethylamine (109-89-7) → (2-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl-ethyl)-diethyl-amine (67489-37-6)

Conditions	Yield
With sodium amide; toluene aufeinanderfolgendes Erhitzen;

1-azaphenothiazine (261-96-1) + 2-(dimethylamino)ethyl chloride (107-99-3) → (2-benzo[b]pyrido[2,3-e][1,4]thiazin-10-yl-ethyl)-dimethyl-amine (67465-69-4)

Conditions	Yield
With sodium amide; xylene
With sodium amide

1-azaphenothiazine (261-96-1) + 3-(Dimethylamino)propyl chloride (109-54-6) → prothipendyl (303-69-5)

Conditions	Yield
With sodium amide; xylene
With sodium amide

Upstream product

• 6631-37-4 2-(phenylamino)pyridine 
• 108-86-1 bromobenzene 
• 13534-89-9 2,3-dibromopyridine 
• 1444-47-9 N-(2-mercaptophenyl) acetamide 
• 137-07-5 2-amino-benzenethiol 
• 7553-56-2 iodine 
• 136-95-8 2-amino-benzthiazole 
• 91902-18-0 2-acetylaminophenyl-(3-nitro-2-pyridyl)sulfide 
• 92316-06-8 2-<(2-aminophenyl)thio>-3-nitropyridine 
• 504-29-0 2-aminopyridine 
• 95873-97-5 10-acetyl-10H-benzo[b]pyrido[2,3-e][1,4]thiazine 

Downstream Products

• 67465-77-4 10-<2-Morpholino-aethyl>-4-aza-phenothiazin 
• 67465-78-5 10-<3-Morpholino-propyl>-4-aza-phenothiazin 
• 482-15-5 isothipendyl 
• 63886-03-3 4-Aza-phenothiazin-10-carbonsaeureaethanolamid 
• 63886-04-4 4-Aza-phenothiazin-10-carbonsaeure-3-methoxy-propyl-amid-1 
• 63906-32-1 4-Aza-phenothiazin-10-carbonsaeure-3-<1-diisopropylamino-propylthioester> 
• 63885-81-4 4-Aza-phenothiazin-10-carbonsaeure-<2-(4-methyl-piperazino)-aethylester> 
• 63885-82-5 4-Aza-phenothiazin-10-carbonsaeure-1-N'-methyl-piperazino-propylester-3 
• 5585-93-3 10-<3-<1-Hydroxyaethyl-piperazinyl-(4)>-propyl>-4-aza-phenothiazin 
• 2167-85-3 benzo[b]pyrido[2,3-e][1,4]thiazine-10-carboxylic acid 2-(2-piperidin-1-yl-ethoxy)-ethyl ester 
• 67465-69-4 10-(2-Dimethylamino-aethyl)-4-aza-phenothiazin 
• 102134-99-6 benzo[b]pyrido[2,3-e][1,4]thiazine-10-carboxylic acid 1-benzyl-piperidin-4-yl ester 
• 1225-65-6 Prothipendyl hydrochloride 
• 1206478-95-6 C₂₇H₂₉N₃O₃S 

Relevant articles and documents

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