4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Base Information

• Chemical Name: 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide
• CAS No.: 1450922-23-2
• Molecular Formula: C₁₉H₁₆F₃N₃O₄S₂
• Molecular Weight: 471.481

Synonyms:4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Chemical Property of 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Chemical Property:

Purity/Quality:

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Technology Process of 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

There total 4 articles about 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide 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:

N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1450923-24-6) + 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (402-07-3) → 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1450922-23-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 130 ℃; for 0.5h; Microwave irradiation; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.05.070

Reference yield:

4-amino-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide (1450923-60-0) → 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1450922-23-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 2.58 h / 0 - 50 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 18 h / 0 - 20 °C

2.2: 5 h / 20 °C

3.1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate / toluene / 0.5 h / 130 °C / Microwave irradiation; Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; borane-THF; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2017.05.070

Reference yield:

3-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide (1450923-58-6) → 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1450922-23-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium trimethylsilanolate / tetrahydrofuran / 1.5 h / 0 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 2.58 h / 0 - 50 °C / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 18 h / 0 - 20 °C

3.2: 5 h / 20 °C

4.1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate / toluene / 0.5 h / 130 °C / Microwave irradiation; Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; borane-THF; sodium trimethylsilanolate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2017.05.070

upstream raw materials:

N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

1-bromo-2-methoxy-4-(trifluoromethyl)benzene

3-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide

4-amino-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide

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