ChemicalBook CAS DataBase List Sulfisoxazole

Sulfisoxazole synthesis

13synthesis methods

Product Name:Sulfisoxazole
CAS Number:127-69-5
Molecular formula:C11H13N3O3S
Molecular Weight:267.3

Sulfisoxazole, N1 -(3,4-dimethyl-5-isoxazolyl)sulfanilamide (33.1.19), is synthesized by reacting 4-acetylaminobenzenesulfonyl chloride with 5-amino-3, 4-dimethylisoxazol (33.1.17), which is in turn synthesized by heterocyclization of 2-methylacetylacetonitrile with hydroxylamine, and subsequent acidic hydrolysis (hydrochloric acid) of the protective acetyl group in the resulting product (33.1.18).

N-(3,4-dimethyl-5-isoxazolyl)-4-nitrobenzenesulfonamide

184644-22-2
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127-69-5
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Yield:127-69-5 69%

Reaction Conditions:

with acetic acid;zinc in acetonitrile at 0 - 20;

Steps:

4.2.2. 4-Amino-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide (14)

Nitro compound 13 (0.71 g, 2.40 mmol) was dissolved in a mixture of AcOH:CH₃CN (20 mL, 1:1, v/v) and cooled to 0 °C. Zn powder (1.5 g) was added in small portions over a period of 10 min. After stirring the reaction for 3 h at rt, reaction mixture was filtered off and filtrate was evaporated to dryness. The resulting residue was purified by silica gel column chromatography (0-10% MeOH in EtOAc, v/v) to afford amine 14 (0.65 g, 69%) as a solid.

References:

Costanzi, Stefano;Santhosh Kumar;Balasubramanian, Ramachandran;Kendall Harden;Jacobson, Kenneth A. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 17,p. 5254 - 5261]

4206-74-0
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127-69-5
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References

19947-75-2
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$14.14/250mgs:

127-69-5
237 suppliers
$5.00/100mg

References

19947-75-2
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$14.14/250mgs:

24939-24-0
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127-69-5
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References

Carbamic acid, (3,4-dimethyl-5-isoxazolyl)-, 1,1-dimethylethyl ester (9CI)

174079-07-3
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127-69-5
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References

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