Methanesulfonamide, N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)-

Base Information

• Chemical Name: Methanesulfonamide, N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)-
• CAS No.: 123663-48-9
• Molecular Formula: C16H14N2O5S
• Molecular Weight: 346.364
• Mol file: 123663-48-9.mol

Synonyms:

Chemical Property of Methanesulfonamide, N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)-

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonamide, N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)-

There total 11 articles about Methanesulfonamide, N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)- 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: 82.1%

3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one (123664-34-6) → N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide (123663-48-9)

Guidance literature:

In water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

5-methoxy-1-nitro-2-phenoxybenzene (84594-95-6) → N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide (123663-48-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C

2: 82 percent / pyridine / 1 h / 20 °C

3: 84 percent / aluminum chloride / CH₂Cl₂ / 1 h / 15 - 20 °C

4: 70 percent aq. HClO₄ / 1 h / 20 °C

5: H₂O / 0.08 h / Heating

6: H₂ / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr

7: 97 percent / Br₂ / CHCl₃ / 0.5 h / 25 - 30 °C

8: 80 percent / NaN₃; DMF / 1 h / 70 - 75 °C

With pyridine; hydrogenchloride; aluminium trichloride; sodium azide; perchloric acid; water; hydrogen; bromine; iron; N,N-dimethyl-formamide; palladium on activated charcoal; In ethanol; dichloromethane; chloroform; acetic acid; 1: Reduction / 2: Mesylation / 3: Acetylation / 4: Cyclization / 5: Hydrolysis / 6: Catalytic hydrogenation / 7: Bromination / 8: amination;

DOI:10.1248/cpb.48.131

Reference yield:

5-methoxy-2-phenoxyaniline (76838-72-7) → N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide (123663-48-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / pyridine / 1 h / 20 °C

2: 84 percent / aluminum chloride / CH₂Cl₂ / 1 h / 15 - 20 °C

3: 70 percent aq. HClO₄ / 1 h / 20 °C

4: H₂O / 0.08 h / Heating

5: H₂ / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr

6: 97 percent / Br₂ / CHCl₃ / 0.5 h / 25 - 30 °C

7: 80 percent / NaN₃; DMF / 1 h / 70 - 75 °C

With pyridine; aluminium trichloride; sodium azide; perchloric acid; water; hydrogen; bromine; N,N-dimethyl-formamide; palladium on activated charcoal; In dichloromethane; chloroform; acetic acid; 1: Mesylation / 2: Acetylation / 3: Cyclization / 4: Hydrolysis / 5: Catalytic hydrogenation / 6: Bromination / 7: amination;

DOI:10.1248/cpb.48.131

upstream raw materials:

3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

5-methoxy-1-nitro-2-phenoxybenzene

5-methoxy-2-phenoxyaniline

2-chloro-5-methoxynitrobenzene

Downstream raw materials:

Iguratimod

Refernces

• 1、 -. "4H-1-benzopyran-4-one derivative or its salt, process for producing the same and pharmaceutical composition comprising the same as active ingredient". . . Retrieved 2008/06/13.