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Chemical Structure| 21312-10-7 Chemical Structure| 21312-10-7
Chemical Structure| 21312-10-7

N4-Acetylsulfamethoxazole

CAS No.: 21312-10-7

N4-Acetylsulfamethoxazole (Acetylsulfamethoxazole) is a metabolite of sulfamethoxazole, a sulfonamide antibiotic used for bacterial infections.

Synonyms: Acetylsulfamethoxazole; STX 606; N-acetyl Sulfamethoxazole

4.5 *For Research Use Only !

Cat. No.: A134633 Purity: 98+%

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Product Details of N4-Acetylsulfamethoxazole

CAS No. :21312-10-7
Formula : C12H13N3O4S
M.W : 295.31
SMILES Code : CC(NC1=CC=C(S(=O)(NC2=NOC(C)=C2)=O)C=C1)=O
Synonyms :
Acetylsulfamethoxazole; STX 606; N-acetyl Sulfamethoxazole
MDL No. :MFCD00205417
InChI Key :GXPIUNZCALHVBA-UHFFFAOYSA-N
Pubchem ID :65280

Safety of N4-Acetylsulfamethoxazole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of N4-Acetylsulfamethoxazole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 21312-10-7 ]

[ 21312-10-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1072-67-9 ]
  • [ 121-60-8 ]
  • [ 21312-10-7 ]
YieldReaction ConditionsOperation in experiment
59% at 20℃; for 12 h; A mixture of 4-acetamidobenzene-1-sulfonyl chloride (4.27 mmol), 5-methylisoxazol-3-amine (4.49 mmol) and DMAP (0.21 mmol) in anhydrous pyridine (10 mL) was stirred at room temperature for 12 h.
After completion of reaction, solvent was evaporated to dryness and diluted with water and extracted with ethyl acetate.
The combined organic layers were washed with water and 1 M aqueous HCl, dried over anhydrous Na2SO4, filtered, and concentrated under vacuum.
The solid residue obtained was purified with flash column chromatography using heptanes to EtOAc (50-100percent) gradient elution to afford the compound 2. 4.2.1
N-(4-(N-(5-Methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide (2)
Yield: 59percent; ESIMS m/z calcd for C12H13N3O4S [M + H]+, 296.07; found 296.06; 1H NMR (400 MHz, (CD3)2SO): δ 11.30 (bs, 1H), 10.35 (bs, 1H), 7.79-7.73 (m, 4H), 6.12 (s, 1H), 2.29 (s, 3H), 2.07 (s, 3H).
13C (100 MHz, (CD3)2SO): δ 170.71, 169.57, 158.07, 144.01, 133.36, 128.50, 119.15, 95.84, 24.57, 12.48.
References: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 1, p. 12 - 17.
[2] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 595 - 603.
[3] Shionogi Kenkyusho Nenpo, 1957, # 7, p. 301,304[4] Chem.Abstr., 1957, p. 17889.
[5] Patent: US2888455, 1957, , .
[6] Crystal Growth and Design, 2013, vol. 13, # 9, p. 4002 - 4016.
[7] Patent: CN105884705, 2016, A, . Location in patent: Paragraph 0013; 0016; 0021; 0026; 0031.
  • 2
  • [ 723-46-6 ]
  • [ 75-36-5 ]
  • [ 21312-10-7 ]
References: [1] Research on Chemical Intermediates, 2012, vol. 38, # 1, p. 77 - 89.
[2] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
  • 3
  • [ 98-74-8 ]
  • [ 21312-10-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
[2] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
  • 4
  • [ 29699-89-6 ]
  • [ 21312-10-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
[2] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
  • 5
  • [ 723-46-6 ]
  • [ 108-24-7 ]
  • [ 21312-10-7 ]
References: [1] Chemosphere, 2004, vol. 57, # 11, p. 1733 - 1738.
[2] Journal of Pharmacology and Experimental Therapeutics, 2006, vol. 319, # 1, p. 488 - 496.
  • 6
  • [ 97254-40-5 ]
  • [ 21312-10-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
  • 7
  • [ 99447-77-5 ]
  • [ 21312-10-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 572 - 575.
  • 8
  • [ 103-84-4 ]
  • [ 21312-10-7 ]
References: [1] Patent: CN105884705, 2016, A, .
 

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