(S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

Base Information

• Chemical Name: (S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide
• CAS No.: 160982-13-8
• Molecular Formula: C10H14ClNO4S2
• Molecular Weight: 311.81
• Hs Code.: 2934999090
• European Community (EC) Number: 870-397-0
• DSSTox Substance ID: DTXSID90432957
• Wikidata: Q72453385
• Mol file: 160982-13-8.mol

Synonyms:160982-13-8;(S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide;(4S)-6-chloro-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazin-4-ol;(4S)-6-Chloro-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazin-4-ol 1,1-Dioxide;SCHEMBL2726839;DTXSID90432957;AKOS016843378;(S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine1,1-dioxide;A883153;(4S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione;(S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide;(S)-6-Chloro-2-(3-methoxy-propyl)-1,1-dioxo-1,2,3,4-tetrahydro-1lambda*6*-thieno[3,2-e][1,2]thiazin-4-ol;(S)-6-chloro-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazin-4-ol 1, 1-dioxide

Chemical Property of (S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

Chemical Property:

• Boiling Point: 466.142 °C at 760 mmHg
• PKA: 12.52±0.20(Predicted)
• Flash Point: 235.714 °C
• PSA: 103.46000
• Density: 1.49 g/cm³
• LogP: 2.49440
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 311.0052780
• Heavy Atom Count: 18
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

(4S)-6-Chloro-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazin-4-ol1,1-Dioxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCCN1CC(C2=C(S1(=O)=O)SC(=C2)Cl)O
• Isomeric SMILES: COCCCN1C[C@H](C2=C(S1(=O)=O)SC(=C2)Cl)O
• Uses: An intermediate in the preparation of Brinzolamide

Technology Process of (S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

There total 7 articles about (S)-6-Chloro-4-hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-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: 94.0%

(S)-3,4-dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (160982-16-1,171274-01-4) + 4,4'-dibromo-di-n-butyl ether (7239-41-0) → (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide (160982-13-8)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide;

DOI:10.1021/op9802125

Reference yield:

3-acetyl-5-chloro-2-thiophenesulfenamide → (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide (160982-13-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tungstate (VI) dihydrate; dihydrogen peroxide / water / 19 h / 15 - 35 °C

2.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale

3.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere

3.2: 2 h / 0 - 22 °C

4.1: potassium carbonate / dimethyl sulfoxide

With sodium tungstate (VI) dihydrate; pyridinium hydrobromide perbromide; sulfuric acid; dihydrogen peroxide; potassium carbonate; B-chlorodiisopinocampheylborane; In tert-butyl methyl ether; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/op9802125

Reference yield:

3-acetyl-5-chloro-2-thiophenesulfonamide (160982-10-5) → (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide (160982-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale

2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere

2.2: 2 h / 0 - 22 °C

3.1: potassium carbonate / dimethyl sulfoxide

With pyridinium hydrobromide perbromide; sulfuric acid; potassium carbonate; B-chlorodiisopinocampheylborane; In tert-butyl methyl ether; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/op9802125

upstream raw materials:

3-acetyl-5-chloro-2-thiophenesulfonamide

3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide

3-acetyl-2,5-dichlorothiophene

(S)-3,4-dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide

Downstream raw materials:

(S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide

brinzolamide

brinzolamide

Refernces