29462-18-8

Basic information

• Product Name: Bentazepam
• Synonyms: Bentazepam;1,3,6,7,8,9-Hexahydro-5-phenyl-2H-[1]benzothieno[2,3-e]-1,4-diazepin-2-one;CI-718;QM-6008;Thiadipon;Thiadipone
• CAS NO: 29462-18-8
• Molecular Formula: C₁₇H₁₆N₂OS
• Molecular Weight: 296.41
• Mol File: 29462-18-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 249.5°C
• Boiling Point: 197.5°C (rough estimate)
• Flash Point: 275.9°C
• Appearance: /
• Density: 1.1654 (rough estimate)
• Vapor Pressure: 2E-11mmHg at 25°C
• Refractive Index: 1.7400 (estimate)
• PKA: 13.24±0.40(Predicted)
• CAS DataBase Reference: Bentazepam(CAS DataBase Reference)
• NIST Chemistry Reference: Bentazepam(29462-18-8)
• EPA Substance Registry System: Bentazepam(29462-18-8)

Safety Data

• Hazardous Substances Data: 29462-18-8(Hazardous Substances Data)

Usage

Originator

Bentazepam,Laboratorios Made S. A.

Uses

Sedative-hypnotic.

Manufacturing Process

To a solution of 3.4 kg N-phthalimidoacetic acid in 20 L of methylene chloride was added a solution of 2.8 kg of 1,1-carbonyl diimidazol in 20 L of methylene chloride. The mixture was refluxed for 1 hour. After cooling to the obtained solution was added a solution of 4.3 kg of 2-amino-3-benzoyl-4,5- tetramethylene thiophene in 30 L of methylene chloride and the reaction mixture was refluxed for 16 hours. After cooling the mixture was washed with 30 L of water, dried with sodium sulfate and filtered. After removing the solvent was obtained the 2-(N-phthalimidoacetylamino)-3-benzoyl-4,5- tetramethylene thiophene, yield 70%, melting point 230°C.

Therapeutic Function

Anticonvulsant, Tranquilizer

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of SOx and NOx.

InChI:InChI=1/C17H16N2OS/c20-14-10-18-16(11-6-2-1-3-7-11)15-12-8-4-5-9-13(12)21-17(15)19-14/h1-3,6-7,18H,4-5,8-10H2

Synthetic route

3-(imino-phenyl-methyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-ylamine + glycine ethyl ester hydrochloride (623-33-6) → bentazepam (29462-18-8)

Conditions	Yield
With pyridine

(E)-3-amino-3-phenyl-2-(2-thioxo-cyclohexyl)-acrylonitrile (43215-25-4) + glycine ethyl ester hydrochloride (623-33-6) → bentazepam (29462-18-8)

Conditions	Yield
With pyridine

[2-(2-bromo-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl]-phenyl-methanone (29462-27-9) → bentazepam (29462-18-8)

Conditions	Yield
With ammonia In methanol; diethyl ether Ambient temperature;

glycine 3-benzoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-ylamide (41042-86-8) → bentazepam (29462-18-8)

Conditions	Yield
With acetic acid In pyridine; benzene

bentazepam (29462-18-8) → 5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepine-2-thione (40054-65-7)

Conditions	Yield
With tetraphosphorus decasulfide In pyridine Heating;
With pyridine; tetraphosphorus decasulfide for 1h;

bentazepam (29462-18-8) + methyl iodide (74-88-4) → 1-methyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one (29462-23-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; paraffin
(i) NaH, DMF, (ii) /BRN= 969135/; Multistep reaction;

bentazepam (29462-18-8) + AllHal → 1-allyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one (50509-63-2)

Conditions	Yield
(i) NaH, DMF, (ii) AllHal; Multistep reaction;

bentazepam (29462-18-8) + 3-halo-propyne → 5-phenyl-1-prop-2-ynyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one (50509-64-3)

Conditions	Yield
(i) NaH, DMF, (ii) 3-halo-propyne; Multistep reaction;

bentazepam (29462-18-8) + nBuHal → 1-butyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one (50509-65-4)

Conditions	Yield
(i) NaH, DMF, (ii) nBuHal; Multistep reaction;

bentazepam (29462-18-8) + PhCH2Hal → 1-benzyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one (50509-66-5)

Conditions	Yield
(i) NaH, DMF, (ii) PhCH2Hal; Multistep reaction;

bentazepam (29462-18-8) → 6-phenyl-7,8,9,10-tetrahydro-4H-benzo[4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (40054-80-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: P2S5, Py / 1 h 2: N2H4*H2O / methanol / Ambient temperature 3: H2SO4 / ethanol / 5 h / Heating View Scheme

bentazepam (29462-18-8) → 5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one hydrazone (40054-52-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: P2S5, Py / 1 h 2: N2H4*H2O / methanol / Ambient temperature View Scheme

Upstream product

• 29462-27-9 [2-(2-bromo-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl]-phenyl-methanone 
• 43215-25-4 (E)-3-amino-3-phenyl-2-(2-thioxo-cyclohexyl)-acrylonitrile 
• 623-33-6 glycine ethyl ester hydrochloride 
• 41042-86-8 glycine 3-benzoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-ylamide 

Downstream Products

• 40054-52-2 5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one hydrazone 
• 40054-80-6 6-phenyl-7,8,9,10-tetrahydro-4H-benzo[4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine 
• 50509-66-5 1-benzyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one 
• 50509-65-4 1-butyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one 
• 50509-64-3 5-phenyl-1-prop-2-ynyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one 
• 50509-63-2 1-allyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one 
• 29462-23-5 1-methyl-5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one 
• 40054-65-7 5-phenyl-1,3,6,7,8,9-hexahydro-benzo[4,5]thieno[2,3-e][1,4]diazepine-2-thione 

Relevant articles and documents

Synthesis and pharmacological evaluation of 2,3 dihydro 1H thieno[2,3 e][1,4]diazepines

A series of 2,3 dihydro 1H thieno[2,3 e][1,4]diazepines was synthesized and evaluated for CNS activity. A new antianxiety screen for benzodiazepine like drugs was used along with the standard anticonvulsant test. Structure activity relationships are discussed. One compound, 1,3,6,7,8,9 hexahydro 5 phenyl 2H [1]benzothieno[2,3 e][1,4]diazepin 2 one monosulfate (CI 718), is undergoing clinical studies in man.