caroxazone

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Company Name: Nanjing Finetech Chemical Co., Ltd.
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Products Intro: Product Name:Caroxazone
CAS:18464-39-6
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Products Intro: Product Name:Caroxazone
CAS:18464-39-6
Package:100 mg;500 mg Remarks:REAGENT;FOR LABORATORY USE ONLY
Company Name: Hangzhou MolCore BioPharmatech Co.,Ltd.
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Products Intro: Product Name:Caroxazone
CAS:18464-39-6
Purity:NLT 98% Remarks:MC534444
Company Name: J & K SCIENTIFIC LTD.  
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Products Intro: Product Name:Caroxazone
CAS:18464-39-6
Package:100Mg,10Mg
Company Name: Shanghai Hekang Biotechnology Co., Ltd.  
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Products Intro: Product Name:Caroxazone
CAS:18464-39-6
Purity:98+% Package:1g, 5g, 10g, 25g, 100g, 1kg, 1000kg Remarks:C8377
caroxazone Basic information
Product Name:caroxazone
Synonyms:caroxazone;2-Oxo-2H-1,3-benzoxazine-3(4H)-acetamide;F.I.-6654;FI-6654;Surodil;Timostenil;2H-1,3-Benzoxazine-3(4H)-acetamide, 2-oxo-
CAS:18464-39-6
MF:C10H10N2O3
MW:206.2
EINECS:2423451
Product Categories:
Mol File:18464-39-6.mol
caroxazone Structure
caroxazone Chemical Properties
Melting point 203-205°
Boiling point 435.1±45.0 °C(Predicted)
density 1.345±0.06 g/cm3(Predicted)
pka15.73±0.40(Predicted)
Safety Information
RIDADR 3249
HazardClass 6.1(b)
PackingGroup III
MSDS Information
caroxazone Usage And Synthesis
OriginatorTimostenil,Farmitalia,Italy,1975
UsesCaroxazone acts as an irreversible, nonselective MAO inhibitor, displaying antidepressant characteristics.
DefinitionChEBI: Caroxazone is a benzoxazine.
Manufacturing Process37.9 g of ethyl glycinate hydrochloride were dissolved in 400 cc of ethanol and 33.5 g of salicylic aldehyde were added. It is refluxed for half an hour and cooled. 38 cc of triethylamine and 25 g of Raney nickel are then added where after hydrogenation is carried out at room temperature and under atmospheric pressure. After hydrogen adsorption was complete, the mixture was filtered and the alcohol evaporated off. The residue was taken up with acidified water, extracted with ether to eliminate part of the by-products, consisting mainly of o-cresol, then made alkaline with ammonia and extracted with ethyl acetate. The solvent was removed in vacuo and the residue crystallized from ether/petroleum ether. 36.7 g of o-hydroxybenzylaminoacetic acid ethyl ester melting at 47°C are obtained.
20 g of this compound were dissolved in 100 cc of tetrahydrofuran and 100 cc of a 30% solution of phosgene in tetrahydrofuran solution were added. After one night at room temperature, the reaction mixture was dried, taken up with 150 cc of anhydrous pyridine and allowed to stand overnight. The pyridine was then removed in vacuo and the residue dissolved in benzol was washed several times with water and chromatographed over 250 g of alumina. Elution with benzene/petroleum ether yielded 16 g of 4H-3-carboethoxymethyl-1,3- benzoxazine-2-one, melting at 90°-91°C.
5 g of this last compound were dissolved in 120 cc of absolute ethanol and saturated with NH3 at 0°C. It was allowed to stand overnight where after 1.5 g of 4H-3-carboxamidomethyl-1,3-andenzoxazine-2-one, melting at 205°C, were obtained. By evaporation from the mother liquors further quantities of the same product were obtained.
Therapeutic FunctionAntidepressant
caroxazone Preparation Products And Raw materials
Raw materialsAmmonia-->Hydrogen-->PHOSGENE-->Ethyl Glycinate Hcl-->Salicylaldehyde
Tag:caroxazone(18464-39-6) Related Product Information
Ketoconazole alpha-Benzyl-2-oxo-2H-1,3-benzoxazine-3(4H)-acetamide caroxazone