1,2-Benzoxazol-3-ylmethanesulfonimidic acid

Base Information

• Chemical Name: 1,2-Benzoxazol-3-ylmethanesulfonimidic acid
• CAS No.: 68291-97-4
• Molecular Formula: C8H8N2O3S
• Molecular Weight: 212.229
• Hs Code.: 2935904000
• Pharos Ligand ID: F726X4U1N7AW,FKL7HX4Q51BN
• Mol file: 68291-97-4.mol

Synonyms:1,2-benzoxazol-3-ylmethanesulfonimidic acid;Lopac0_001250;BDBM50028010

Chemical Property of 1,2-Benzoxazol-3-ylmethanesulfonimidic acid

Chemical Property:

• Appearance/Colour: off-white powder
• Melting Point: 275°C dec
• Refractive Index: 1.5690 (estimate)
• Boiling Point: 457.2 °C at 760 mmHg
• PKA: 10.2(at 25℃)
• Flash Point: 230.3 °C
• PSA: 94.57000
• Density: 1.509 g/cm³
• LogP: 2.39740
• Storage Temp.: Store at +4°C
• Solubility.: H2O: >5 mg/mL, soluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 212.02556330
• Heavy Atom Count: 14
• Complexity: 314

Purity/Quality:

99% ^*data from raw suppliers

1,2-Benzisoxazole-3-methanesulfonate, Sodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NO2)CS(=N)(=O)O
• Description: Zonisamide is a new generation of sulfonamide anticonvulsant that is primarily used as supplemental therapy in treatment of partial seizures in combination with other antiepileptic medications. Besides, it is approved to be applied as an adjunctive therapy in adults suffering from infantile spasm, mixed seizure types of Lennox–Gastaut syndrome, myoclonic, and generalized tonic clonic seizure. Recent studies have proved that zonisamide can acts as a migraine preventative medication and is effective in several cases of neuropathic pain. In an open-label trial, zonisamide shows positive effects on attenuating the symptoms of tardive dyskinesia. Zonisamide is a second-generation antiepileptic drug (AED) known with the proprietary brand name of Zonegran? (Eisai) in the UK and USA. It is assumed that zonisamide functions on the sodium and calcium channels in the brain cells, in which it controls electric-currents that are responsible for seizure activity. The FDA approved zonisamide in March 2000. Zonisamide is a broad-spectrum antiepileptic effective in the treatment of refractory seizures. In cultured spinal cord neurons, zonisamide blocks the sustained firing of action potentials induced by depolarizing steps of current injected across the membrane.
• Indications: Epilepsy Monotherapy of focal seizures with or without secondary generalization and adjunctive therapy of refractory focal seizures with or without secondary generalization. Recommendations summarized from NICE (2012) Seizure types: on referral to tertiary care (absence seizures, focal seizures, myoclonic seizures). Epilepsy types: on referral to tertiary care (absence syndromes, juvenile myoclonic epilepsy, idiopathic generalized epilepsy, benign epilepsy with centrotemporal spikes, panayiotopoulos syndrome, late- onset childhood occipital epilepsy).
• Uses: anticonvulsant;carbonic anhydrase inhibitor, repetitive firing of voltage-gated sodium channels and reduction of T-type calcium channel currents blocker Sulfonamide antiseizure agent; blocks repetitive firing of voltagesensitive sodium channels and reduces voltage-sensitive T-type calcium currents. Heterocyclic methanesulfonide with anticonvulsant pro perties. The compound is under investigation for potential therapeutic use as an antiepileptic drug. Anticonvulsant. muscarinic antagonist used as an antispasmodic For use as adjunctive treatment of partial seizures in adults with epilepsy.
• Therapeutic Function: Anticonvulsant; Antiepileptic
• Biological Functions: Zonisamide has only recently been approved for use in the United States, although it has been available in Japan for several years. It is effective in partial complex and generalized tonic–clonic seizures and also appears to be beneficial in certain myoclonic seizures. It has a long half-life (about 60 hours) and requires about 2 weeks to achieve steady-state levels. It causes cerebellovestibular side effects similar to those of most other AEDs sharing its mechanism of action. In addition, it appears to cause an increased incidence of kidney stones.
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: anticonvulsant effect antagonised; avoid with St John’s wort. Antimalarials: anticonvulsant effect antagonised by mefloquine. Antipsychotics: anticonvulsant effect antagonised. Orlistat: increased risk of convulsions.

Technology Process of 1,2-Benzoxazol-3-ylmethanesulfonimidic acid

There total 9 articles about 1,2-Benzoxazol-3-ylmethanesulfonimidic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.6%

1,2-benzoxazol-3-ylmethanesulfonyl chloride (73101-65-2) → 1,2-benzisoxazole-3-methanesulfonamide (68291-97-4)

Guidance literature:

With ammonia; In toluene; at 2 - 15 ℃; pH=9;

Reference yield: 85.0%

1,2-benzoxazol-3-ylmethanesulfonyl chloride (73101-65-2) → 1,2-benzisoxazole-3-methanesulfonamide (68291-97-4) + 1,2-benzisoxazole-3-methanesulfonic acid ammonium salt (81534-20-5)

Guidance literature:

With ammonia; In toluene; at 10 - 15 ℃;

Reference yield: 84.6%

→ 1,2-benzisoxazole-3-methanesulfonamide (68291-97-4)

Guidance literature:

With active carbon SX₁; In ethanol; at 2 ℃; for 1.5h; Purification / work up; Heating / reflux;

upstream raw materials:

1,2-benzoxazol-3-ylmethanesulfonyl chloride

1,2-benzisoxazole-3-methanesulfonic acid sodium salt

2-(benzo[d]isoxazol-3-yl)acetic acid

((1-(2-fluorophenyl)vinyl)oxy)trimethylsilane

Downstream raw materials:

2-Sulfamoylacetylphenol

ω-sulfamoyl-2-hydroxyacetophenone imide

C₃₀H₃₉NO₆S

C₂₈H₃₇NO₅S

Refernces

• 1、 -. "Green and environment-friendly zonisamide synthesis method". Paragraph 0040; 0042-0043; 0047; 0049-0050; 0054; 0056-0057. . Retrieved 2017/08/29.
• 2、 -. "PURE 1,2-BENZISOXAZOLE-3-METHANE-SULFONIC ACID SODIUM SALT AND PURIFICATION PROCESS". Page/Page column 13. . Retrieved 2008/06/13.