3-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene

Base Information

• Chemical Name: 3-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene
• CAS No.: 84449-96-7
• Molecular Formula: C27H27NO4S
• Molecular Weight: 461.582
• ChEMBL ID: CHEMBL10486
• DSSTox Substance ID: DTXSID901120050
• Mol file: 84449-96-7.mol

Synonyms:CHEMBL10486;SCHEMBL7621850;PWABRORXEFUSPF-UHFFFAOYSA-N;DTXSID901120050;3-[4-(2-diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene;84449-96-7;[4-[2-(Diethylamino)ethoxy]phenyl][6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]methanone

Chemical Property of 3-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene

Chemical Property:

• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 461.16607952
• Heavy Atom Count: 33
• Complexity: 613

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=O)C2=C(SC3=C2C=CC(=C3)O)C4=CC=C(C=C4)O

Technology Process of 3-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene

There total 8 articles about 3-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene 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: 71.0%

3-[4-(2-diethylaminoethoxy)benzoyl]-6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, hydrochloride (84449-95-6) → <6-hydroxy-2-(4-hydroxyphenyl)benzothien-3-yl><4-<2-(diethylamino)ethoxy>phenyl>methanone (84449-96-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; for 24h; Ambient temperature;

DOI:10.1021/jm00374a021

Reference yield:

α-(3-methoxyphenyl-thio)-4-methoxyacetophenone (63675-73-0) → <6-hydroxy-2-(4-hydroxyphenyl)benzothien-3-yl><4-<2-(diethylamino)ethoxy>phenyl>methanone (84449-96-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / PPA / 1 h / 85 - 90 °C

2: 71 percent / pyridine hydrochloride / 6 h / 220 °C

3: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature

4: 80 percent / AlCl₃ / 1,2-dichloro-ethane / 16 h

5: 71 percent / 5 N aq. NaOH / tetrahydrofuran; methanol / 24 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; aluminium trichloride; pyridine hydrochloride; In tetrahydrofuran; methanol; 1,2-dichloro-ethane;

DOI:10.1021/jm00374a021

Reference yield:

3-methoxybenzenethiol (15570-12-4) → <6-hydroxy-2-(4-hydroxyphenyl)benzothien-3-yl><4-<2-(diethylamino)ethoxy>phenyl>methanone (84449-96-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 80.4 percent / KOH / ethanol; H₂O; ethyl acetate / Ambient temperature

2: 69 percent / PPA / 1 h / 85 - 90 °C

3: 71 percent / pyridine hydrochloride / 6 h / 220 °C

4: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature

5: 80 percent / AlCl₃ / 1,2-dichloro-ethane / 16 h

6: 71 percent / 5 N aq. NaOH / tetrahydrofuran; methanol / 24 h / Ambient temperature

With pyridine; dmap; potassium hydroxide; sodium hydroxide; aluminium trichloride; pyridine hydrochloride; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1021/jm00374a021

upstream raw materials:

3-[4-(2-diethylaminoethoxy)benzoyl]-6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, hydrochloride

3-methoxybenzenethiol

4-(2-(diethylamino)ethoxy)benzoyl chloride

2-(4'-methoxyphenyl)-6-methoxybenzothiophene