7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene

Base Information

• Chemical Name: 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene
• CAS No.: 211758-94-0
• Molecular Formula: C₃₀H₃₈N₂O₄S
• Molecular Weight: 522.709

Synonyms:7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene

Chemical Property of 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene

Chemical Property:

Purity/Quality:

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Technology Process of 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene

There total 15 articles about 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene 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: 97.0%

(4Z,16Z)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(24),4,8,10,12,16,20,22-octaene (211758-87-1) → 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(20),8(13),9,11,21,23-hexaene (211758-94-0)

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; water; for 14.5h; Heating;

DOI:10.1021/jo9801770

Reference yield:

2-methyl-4-nitropyridine N-oxide (5470-66-6) → 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(20),8(13),9,11,21,23-hexaene (211758-94-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 84 percent / PCl₃ / CHCl₃ / 40 h / Ambient temperature

2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

3: 83 percent / methanol / Ambient temperature

4: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.83 h / Ambient temperature

5: 99 percent / Na/Hg, NaH₂PO₄ / methanol / 1 h

6: 1.) n-BuLi / 1.) THF, -78 to -50 deg C, 40 min, 2.) THF, -50 deg C, 5 min, then room temp., 30 min

8: 96 percent / ammonium molybdate, aq. H₂O₂ / ethanol / 17 h

9: 94 percent / aq. HCl / tetrahydrofuran / 8 h / Ambient temperature

10: 1.) LiCl, MsCl, 2,6-lutidine, 2.) NaHMDS / 1.) DMF, room temp., 2 h, 2.) THF, reflux, 2.5 h

11: 97 percent / p-TsNHNH₂, NaOAc / tetrahydrofuran; H₂O / 14.5 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium dihydrogenphosphate; sodium amalgam; n-butyllithium; ammonium molybdate; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; methanesulfonyl chloride; toluene-4-sulfonic acid hydrazide; lithium chloride; phosphorus trichloride; In tetrahydrofuran; methanol; ethanol; hexane; chloroform; water; dimethyl sulfoxide;

DOI:10.1021/jo9801770

Reference yield:

2-methyl-4-nitro-pyridine (13508-96-8) → 7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(20),8(13),9,11,21,23-hexaene (211758-94-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

2: 83 percent / methanol / Ambient temperature

3: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.83 h / Ambient temperature

4: 99 percent / Na/Hg, NaH₂PO₄ / methanol / 1 h

5: 1.) n-BuLi / 1.) THF, -78 to -50 deg C, 40 min, 2.) THF, -50 deg C, 5 min, then room temp., 30 min

7: 96 percent / ammonium molybdate, aq. H₂O₂ / ethanol / 17 h

8: 94 percent / aq. HCl / tetrahydrofuran / 8 h / Ambient temperature

9: 1.) LiCl, MsCl, 2,6-lutidine, 2.) NaHMDS / 1.) DMF, room temp., 2 h, 2.) THF, reflux, 2.5 h

10: 97 percent / p-TsNHNH₂, NaOAc / tetrahydrofuran; H₂O / 14.5 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium dihydrogenphosphate; sodium amalgam; n-butyllithium; ammonium molybdate; dihydrogen peroxide; sodium acetate; sodium hexamethyldisilazane; methanesulfonyl chloride; toluene-4-sulfonic acid hydrazide; lithium chloride; In tetrahydrofuran; methanol; ethanol; hexane; water; dimethyl sulfoxide;

DOI:10.1021/jo9801770

upstream raw materials:

(4Z,16Z)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

2-methyl-4-nitro-pyridine

2-methyl-4-nitropyridine N-oxide

3-Benzenesulfonylmethyl-2-methyl-4-nitro-pyridine

Downstream raw materials:

7-Allyl-7-benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁰⁾,8⁽¹³⁾,9,11,21,23-hexaene

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