ChemicalBook CAS DataBase List Riluzole

Riluzole synthesis

5synthesis methods

Product Name:Riluzole
CAS Number:1744-22-5
Molecular formula:C8H5F3N2OS
Molecular Weight:234.2

461-82-5 Synthesis

461-82-5
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333-20-0
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$13.50/100G

1744-22-5
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$5.00/250mg

Yield:1744-22-5 94%

Reaction Conditions:

Stage #1:4-(trifluoromethoxy)aniline;potassium thioacyanate in acetic acid at 20; for 0.333333 h;
Stage #2: with bromine in acetic acid at 20;

Steps:

1.2. General procedure for the synthesis of 6-(trifluoromethoxy)benzo[d]thiazol-2-amine (1)
Potassium thiocyanate (40 mmol)was added to a solution of 4-(trifluoromethoxy)aniline (10 mmol)in glacial acetic acid (20 mL). After the mixture stirring for 20 minat r. t., the reaction was cooled down just to keep the solution liquid. The solutionof bromine (15 mmol) in glacial acetic acid (5 mL) was added dropwiseover the 30 min. The reaction was allowed to reach r. t. and stirred overnight.The mixture was diluted with H₂O, alkalized with Na₂CO₃and extracted with ethyl acetate (3 x 50 mL). The combined organiclayers were dried over Na₂SO₄, filtered and the solventwas under reduced pressure to dryness. The residue was recrystallized from diethylether-petrol ether to yield 6-(trifluoromethoxy)benzo[d]thiazol-2-amine as light-yellow solid(94%). ¹H and ¹³C NMR, melting point and analytical data werein agreement with those reported in literature.

References:

Hroch, Lukas;Benek, Ondrej;Guest, Patrick;Aitken, Laura;Soukup, Ondrej;Janockova, Jana;Musil, Karel;Dohnal, Vlastimil;Dolezal, Rafael;Kuca, Kamil;Smith, Terry K;Gunn-Moore, Frank;Musilek, Kamil [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 15,p. 3675 - 3678] Location in patent:supporting information

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461-82-5 Synthesis

461-82-5
448 suppliers
$10.00/1g