N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE

Base Information

• Chemical Name: N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE
• CAS No.: 120298-38-6
• Molecular Formula: C₁₀H₁₄N₂O₅S₃
• Molecular Weight: 338.43
• Mol file: 120298-38-6.mol

Synonyms:Acetamide,N-[2-(aminosulfonyl)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-yl]-,S,S-dioxide; 4H-Thieno[2,3-b]thiopyran, acetamide deriv.

Chemical Property of N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.647
• PSA: 171.89000
• Density: 1.538[at 20℃]
• LogP: 3.84080
• Water Solubility.: 440mg/L at 20℃

Purity/Quality:

99.9% ^*data from raw suppliers

N-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-ylacetamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 43-50/53
• Safety Statements: 24-37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(6S)-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl]acetamide is an intermediate in the synthesis of dorzolamide, an carbonic anhydrase inhibitor with antiglaucoma properties.

Technology Process of N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE

There total 25 articles about N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE 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%

5,6-dihydro-4-hydroxy-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (154802-22-9) + acetonitrile (75-05-8,26809-02-9) → 4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (120298-38-6)

Guidance literature:

With sulfuric acid; at 0 - 30 ℃; for 25 - 27h;

Reference yield:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (154802-22-9) → (4S,6S)?4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (147200-03-1,120298-38-6) + cis-(6S)-4-acetylammino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (147128-79-8,120298-38-6)

Guidance literature:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide; With methanesulfonic acid; In water; acetonitrile; at 10 - 87 ℃; for 19h; Inert atmosphere; Reflux;

With ammonium hydroxide; In water; acetonitrile; at 7 - 40 ℃; for 4h; pH=7.3; Overall yield = 91.1 %; Overall yield = 20.6 g; Optical yield = 58 %de;

Reference yield:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (154802-22-9) → (4S,6S)?4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (147200-03-1,120298-38-6) + cis-(6S)-4-acetylammino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide (147128-79-8,120298-38-6)

Guidance literature:

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide; With methanesulfonic acid; In water; acetonitrile; at 10 - 87 ℃; for 19h; Inert atmosphere; Reflux;

With ammonium hydroxide; In water; acetonitrile; at 7 - 40 ℃; for 4h; pH=7.3; Overall yield = 91.1 %; Overall yield = 20.6 g; Optical yield = 58 %de;

upstream raw materials:

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran

(S)-3-(thien-2-ylthio)butyric acid

(S)-6-Methyl-6H-thieno[2,3-b]thiopyran 7,7-dioxide

Downstream raw materials:

dorzolamide

Refernces

• 1、 -. "PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED OXAMIDES". Page/Page column 13; 14. . Retrieved 2014/01/18.
• 2、 -. "PROCESS FOR PREPARING DORZOLAM IDE". Page/Page column 14; 18-19. . Retrieved 2009/01/20.