63547-13-7 Usage
Description
Adrafinil is a centrally-acting,
αl-adrenergic agonist useful in the management of
vigillance disturbances and depression in the elderly.
Chemical Properties
Light Pink Solid
Originator
Labs. L. Lafon (France)
Uses
Different sources of media describe the Uses of 63547-13-7 differently. You can refer to the following data:
1. a-Adrenergic agonist. Treatment of depression
2. α-Adrenergic agonist. Treatment of depression.
Manufacturing Process
7.6 g (0.1 mol) of thiourea and 100 ml of dematerialized water are introduced
into a 500 ml three-neck flask equipped with a magnetic stirrer, a dropping
funnel and a condenser; the mixture is heated to 50°C and 20.25 g (18 ml;
0.1 mol) of chlorodiphenylmethane are then added all at once. The solution is
left refluxing until it has become limpid, and is then cooled to 20°C, and 200
ml of 2.5 N NaOH are added dropwise. So the sodium benzhydrylthiolate is
obtained.
A solution of sodium 3-chloroacetate is added to the solution of sodium
benzhydrylthiolate at about 60°C. Thereafter the temperature is raised to the
boil, the mixture is left under reflux for about 0.5 h and is then cooled,
filtered over charcoal and acidified with concentrated HCl, and 3-
(benzhydrylthio)acetic acid are thus precipitated.
To the solution of 3-(benzhydrylthio)acetic acid in 1,2-dichloroethane,
methanol and concentrated H2SO4 have been added. The whole is heated to
the reflux temperature for about 5 h, cooled, and decanted, the aqueous
phase is discarded and the organic phase is washed with a saturated sodium
bicarbonate solution and then with water until the wash waters have a neutral
pH. After drying over MgSO4 and evaporating the solvent, the 3-
(benzhydrylthio)acetic acid methyl ester is obtained.
The 3-(benzhydrylthio)acetic acid methyl ester dissolved in methanol, is added
to a solution of hydroxylamine base [prepared by neutralising 0.15 mol (10.4
g) of hydroxylamine hydrochloride with 0.15 mol of sodium methylate]. The
whole is left at ordinary temperature (15°-25°C) for 48 h, the sodium chloride
is filtered off, the methanol is evaporated, the residue is taken up with
aqueous alkali, the solution is filtered over charcoal, the filtrate is acidified
with concentrated HCl, and the 3-(benzhydrylthio)acethylhydroxamic acid
(recrystallised from benzene) is thus obtained.
The 3-(benzhydrylthio)acethylhydroxamic acid, dissolved in anhydrous
CH3COOH, is reacted with H2O2. The mixture is left at 40°-45°C for about 1.5
h, the acetic acid is evaporated and the residue is taken up in 50 ml of ethyl
acetate; the 2-[(diphenylmethyl)sulfinyl]-N-hydroxyacetamide (CRL 40028)
crystallises (recrystallised from isopropanol).
Brand name
OLMIFON
Check Digit Verification of cas no
The CAS Registry Mumber 63547-13-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,3,5,4 and 7 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 63547-13:
(7*6)+(6*3)+(5*5)+(4*4)+(3*7)+(2*1)+(1*3)=127
127 % 10 = 7
So 63547-13-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17)
63547-13-7Relevant articles and documents
Synthesis and determination of the absolute configuration of the enantiomers of modafinil
Prisinzano, Thomas,Podobinski, John,Tidgewell, Kevin,Luo, Min,Swenson, Dale
, p. 1053 - 1058 (2007/10/03)
The asymmetric synthesis of both enantiomers of modafinil, a unique CNS stimulant with a reduced abuse liability, is described. This approach effectively prepares modafinil on a multigram scale in several steps from benzhydrol. The described synthetic route has also been used to produce the more water soluble analogue, adrafinil. X-ray crystallographic analysis on (-)-(diphenylmethanesulfinyl)acetic acid has determined the absolute configuration to be R.
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