5-[[(2-Hydroxyethyl)amino]methyl]thieno[2,3-b]thiophene-2-sulfonamide

Base Information

• Chemical Name: 5-[[(2-Hydroxyethyl)amino]methyl]thieno[2,3-b]thiophene-2-sulfonamide
• CAS No.: 122266-93-7
• Molecular Formula: C₉H₁₂N₂O₃S₃
• Molecular Weight: 292.404
• ChEMBL ID: CHEMBL1194579
• DSSTox Substance ID: DTXSID00560614
• Nikkaji Number: J412.641F
• Wikidata: Q82444074
• Mol file: 122266-93-7.mol

Synonyms:122266-93-7;5-[[(2-Hydroxyethyl)amino]methyl]thieno[2,3-b]thiophene-2-sulfonamide;2-[(2-hydroxyethylamino)methyl]thieno[2,3-b]thiophene-5-sulfonamide;5-{[(2-Hydroxyethyl)amino]methyl}thieno[2,3-b]thiophene-2-sulfonamide;SCHEMBL9529186;CHEMBL1194579;DTXSID00560614

Chemical Property of 5-[[(2-Hydroxyethyl)amino]methyl]thieno[2,3-b]thiophene-2-sulfonamide

Chemical Property:

• PSA: 157.28000
• LogP: 2.86410
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 292.00100577
• Heavy Atom Count: 17
• Complexity: 357

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(SC2=C1C=C(S2)S(=O)(=O)N)CNCCO

Technology Process of 5-[[(2-Hydroxyethyl)amino]methyl]thieno[2,3-b]thiophene-2-sulfonamide

There total 11 articles about 5-[[(2-Hydroxyethyl)amino]methyl]thieno[2,3-b]thiophene-2-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:

5-{[(E)-2-Hydroxy-ethylimino]-methyl}-thieno[2,3-b]thiophene-2-sulfonic acid amide → 5-(2-hydroxyethylaminomethyl)thieno[2,3-b]thiophene-2sulfonamide (122266-93-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 0.5h;

DOI:10.1021/jm00110a008

Reference yield:

2-Formylthieno<2,3-b>thiophene (31486-85-8) → 5-(2-hydroxyethylaminomethyl)thieno[2,3-b]thiophene-2sulfonamide (122266-93-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C

3: concd. NH₄OH / acetone / 1.5 h

4: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature

5: HCl / methanol / 0.08 h / Heating

6: NaBH₄ / methanol; tetrahydrofuran / 0.5 h

With hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; toluene-4-sulfonic acid; trimethyl orthoformate; In tetrahydrofuran; methanol; acetone; toluene;

DOI:10.1021/jm00110a008

Reference yield:

methyl thieno[2,3-b]thiophene-2-carboxylate (20969-37-3) → 5-(2-hydroxyethylaminomethyl)thieno[2,3-b]thiophene-2sulfonamide (122266-93-7)

Guidance literature:

Multi-step reaction with 8 steps

1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature

2: 13.10 g / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

3: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C

5: concd. NH₄OH / acetone / 1.5 h

6: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature

7: HCl / methanol / 0.08 h / Heating

8: NaBH₄ / methanol; tetrahydrofuran / 0.5 h

With hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; toluene-4-sulfonic acid; pyridinium chlorochromate; trimethyl orthoformate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1021/jm00110a008

upstream raw materials:

2-Formylthieno<2,3-b>thiophene

methyl thieno[2,3-b]thiophene-2-carboxylate

methyl <(3-formylthiophene-2-yl)thio>acetate

2-(thiophen-3-yl)-1,3-dioxolane

Refernces