5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole

Base Information

• Chemical Name: 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole
• CAS No.: 1170192-98-9
• Molecular Formula: C₁₁H₉NO₂S₂
• Molecular Weight: 251.33

Synonyms:5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole

Chemical Property of 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole

Chemical Property:

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Technology Process of 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole

There total 3 articles about 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole 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: 38.0%

2-bromomethyl-5-phenylthiophen-3-sulfonamide (1170192-95-6) → 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole (1170192-98-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 55 ℃;

DOI:10.1016/j.bmcl.2013.01.120

Reference yield:

methyl 3-amino-5-phenylthiophene-2-carboxylate (100063-22-7) → 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole (1170192-98-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium nitrate; sulfur dioxide; hydrogenchloride / water

1.2: 0 °C

2.1: ammonia / 1,4-dioxane / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

4.1: triphenylphosphine; carbon tetrabromide / tetrahydrofuran; dichloromethane / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 55 °C

With hydrogenchloride; sodium nitrate; lithium aluminium tetrahydride; carbon tetrabromide; sulfur dioxide; ammonia; sodium hydride; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.01.120

Reference yield:

5-phenyl-3-chlorosulfonyl-2-methoxycarbonyl thiophene (113387-58-9) → 5-phenyl-1,1-dioxo-2,3-dihydrothieno[2,3-d]isothiazole (1170192-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonia / 1,4-dioxane / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

3: triphenylphosphine; carbon tetrabromide / tetrahydrofuran; dichloromethane / 20 °C

4: sodium hydride / N,N-dimethyl-formamide / 55 °C

With lithium aluminium tetrahydride; carbon tetrabromide; ammonia; sodium hydride; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.01.120

upstream raw materials:

2-bromomethyl-5-phenylthiophen-3-sulfonamide

methyl 3-amino-5-phenylthiophene-2-carboxylate

5-phenyl-3-chlorosulfonyl-2-methoxycarbonyl thiophene

Downstream raw materials:

Ethyl 3-methyl-2-(5-phenyl-1,1-dioxothieno[2,3-d]isothiazol-2(3H)-yl)butyrate

C₁₆H₁₇NO₄S₂

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