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57801-81-7

57801-81-7 Structure

57801-81-7 Structure
IdentificationBack Directory
[Name]

BROTIZOLAM
[CAS]

57801-81-7
[Synonyms]

we941
WE 941
Lendorm
Sintonal
Lendormin
WE 941-BS
Mederantil
BROTIZOLAM
)-9-methyl-
Mederantil:Sintoml
BROTIZOLAM USP/EP/BP
UMSGKTJDUHERQW-UHFFFAOYSA-N
Brotizolam (1.0mg/ml in Acetonitrile)
2-bromo-4-(2-chlorophenyl)-9-methyl-6h-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1
8-bromo-6-(o-chlorophenyl)-1-methyl-4h-s-triazolo(3,4c)thieno(2,3e)-1,4-diaz
6h-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine,2-bromo-4-(2-chlorophenyl
2-Bromo-4-(o-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-s-triazolo[4,3-a]-[1,4]diazepine
2-Bromo-4-(o-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
2-Bromo-4-(2-chlorophenyl)-9-methyl-6H-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine
2-Bromo-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-α][1,4]diazepine
6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine, 2-bromo-4-(2-chlorophenyl)-9-methyl-
[EINECS(EC#)]

260-964-5
[Molecular Formula]

C15H10BrClN4S
[MDL Number]

MFCD00867545
[MOL File]

57801-81-7.mol
[Molecular Weight]

393.69
Chemical PropertiesBack Directory
[Melting point ]

204-206?C
[Boiling point ]

561.3±60.0 °C(Predicted)
[density ]

1.6265 (estimate)
[storage temp. ]

-20°C Freezer
[solubility ]

Practically insoluble in water, sparingly soluble or slightly soluble in methanol, slightly soluble in ethanol (96 per cent).
[form ]

A crystalline solid
[pka]

2.01±0.40(Predicted)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Dichloromethane-->Chloroform-->Phosphorus pentasulfide-->Triethyl orthoacetate-->Hexamethyleneimine-->Hydrazine hydrate
Hazard InformationBack Directory
[Description]

Brotizolam is a hypnotic/sedative approximately 60-100 times more potent than flurazepam. As with other short-acting, annulated benzodiazepines (e.g., triazolam), cited advantages include lack of adverse effects on sleep and performance after arousal.
[Chemical Properties]

Tan Solid
[Originator]

Boehringer Ingelheim (W. Germany)
[Uses]

A hypnotic and a sedative, also used in veterinary medicine as an appetite stimulant
[Definition]

ChEBI: Brotizolam is an organic molecular entity.
[Manufacturing Process]

(a) 11.5 g of 7-bromo-5-(o-chlorophenyl)-3H-[2,3e]-thieno-1,4-diazepin-2- one (see German Patent 2,221,623), were heated at 55° to 60°C with 100 cc of absolute pyridine and 6.5 g of phosphorus pentasulfide for 4 hours while stirring. The mixture was allowed to cool and was then poured into 100 cc of saturated ice-cold NaCl solution. The precipitate was collected by suction filtration, washed with water, dissolved in 100 cc of methylene chloride, the solution was dried and evaporated, and the residue was treated with a little methylene chloride. After suction filtration, 6 g of brown crystalline 7-bromo- 5-(o-chlorophenyl)-3H-[2,3e]-thieno-1,4-diazepine-2-thione, melting point 214°C (decomposition) were obtained.
(b) 6.0 g of this compound were suspended in 100 cc of tetrahydrofuran, and the suspension was stirred at room temperature with 1.2 g of hydrazine hydrate for 20 minutes. After evaporation to about 10 cc, 20 cc of ether were added, and the crystals were collected by suction filtration. Yield: 5.2 g of 7- bromo-5-(o-chlorophenyl)-2-hydrazino-3H-[2,3e]-thieno-1,4-diazepine, melting point about 300°C (decomposition).
(c) 5.2 g of this compound were suspended in 50 cc of orthotriethyl acetate, and the suspension was heated to 80°C. After about 30 minutes a clear solution was first formed from which later colorless crystals separated out. The mixture was allowed to cool, and the crystals were collected by suction filtration and washed with ether. Yield: 5 g of the compound, melting point 211° to 213°C.
[Brand name]

Lendorm (Boehringer Ingelheim);LENDORMIN.
[Therapeutic Function]

Psychotropic
Safety DataBack Directory
[Toxicity]

LD50 in mice, rats (mg/kg): >10000, >10000 orally; 920, 1000 i.p. (Hewett)
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