6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide

Base Information

• Chemical Name: 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide
• CAS No.: 1586025-42-4
• Molecular Formula: C₂₁H₂₂N₂O₅S
• Molecular Weight: 414.482

Synonyms:6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide

Chemical Property of 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide

Chemical Property:

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Technology Process of 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide

There total 7 articles about 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide 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: 98.0%

methyl 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate (1586025-51-5) → 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide (1586025-42-4)

Guidance literature:

With hydroxylamine; In methanol; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1002/cmdc.201300270

Reference yield:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene (63675-74-1) → 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide (1586025-42-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bromine / chloroform / 0.17 h / 50 °C / Inert atmosphere

2.1: n-butyllithium / hexane / 2 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

2.3: Inert atmosphere

3.1: thionyl chloride / toluene / 2 h / Reflux; Inert atmosphere

4.1: triethylamine / dichloromethane / 24 h / 0 °C / Inert atmosphere

5.1: boron tribromide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: hydrogenchloride / Reflux; Inert atmosphere

7.1: hydroxylamine / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; thionyl chloride; hydroxylamine; bromine; boron tribromide; triethylamine; In methanol; hexane; dichloromethane; chloroform; toluene;

DOI:10.1002/cmdc.201300270

Reference yield:

3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (176672-06-3) → 6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide (1586025-42-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / hexane / 2 h / -78 °C / Inert atmosphere

1.2: Inert atmosphere

1.3: Inert atmosphere

2.1: thionyl chloride / toluene / 2 h / Reflux; Inert atmosphere

3.1: triethylamine / dichloromethane / 24 h / 0 °C / Inert atmosphere

4.1: boron tribromide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: hydrogenchloride / Reflux; Inert atmosphere

6.1: hydroxylamine / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; thionyl chloride; hydroxylamine; boron tribromide; triethylamine; In methanol; hexane; dichloromethane; toluene;

DOI:10.1002/cmdc.201300270

upstream raw materials:

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

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate

3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate

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