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Sulfalen synthesis
- Product Name:Sulfalen
- CAS Number:152-47-6
- Molecular formula:C11H12N4O3S
- Molecular Weight:280.3
This same 3-methoxy-2-aminopyrazine (33.1.36) is synthesized from 3-hydroxypyrazin- 2-carboxamide. Reacting this with phosphorous oxychloride replaces the hydroxyl group with a chlorine atom while the carboxamide group simultaneously undergoes dehydration to form 3-chloro-2-cyanopyrazine (33.1.37). Next, reacting this with sodium methoxide gives 3-methoxy-2-cyanopyrazine (33.1.38). The cyano group in this compound is hydrolyzed by a base in the presence of hydrogen peroxide to a carboxamide group, giving 3-methoxy-2-carboxamideopyrazine (33.1.39). The resulting product undergoes a Hofmann rearrangement when reacted with sodium hypochlorite, giving the desired 3-methoxy-2 aminopyrazine (33.1.36). Reacting this with 4-acetylaminobenzenesulfonyl chloride and subsequent hydrolysis of the acetyl group with a base to (33.1.40) gives sulfalene.
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4774-10-1
108 suppliers
$15.00/100mg
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121-60-8
339 suppliers
$10.00/1g
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152-47-6
198 suppliers
$5.00/100mg
Yield:-
Steps:
Multi-step reaction with 2 steps
1: pyridine
2: sodium hydroxide / water
References:
Perlovich, German L.;Ryzhakov, Alex M.;Tkachev, Valery V.;Hansen, Lars Kr.;Raevsky, Oleg A. [Crystal Growth and Design,2013,vol. 13,# 9,p. 4002 - 4016]
![Acetamide, N-[4-[[(3-methoxy-2-pyrazinyl)amino]sulfonyl]phenyl]-](/CAS/20200401/GIF/655-78-7.gif)
655-78-7
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152-47-6
198 suppliers
$5.00/100mg

4774-10-1
108 suppliers
$15.00/100mg

152-47-6
198 suppliers
$5.00/100mg