2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Base Information

• Chemical Name: 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
• CAS No.: 60681-99-4
• Molecular Formula: C12H16ClNO4
• Molecular Weight: 273.716
• UNII: VCL6EW672N
• DSSTox Substance ID: DTXSID60463490
• Mol file: 60681-99-4.mol

Synonyms:60681-99-4;2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide;VCL6EW672N;2-Chloro-N-(2-(2,5-dimethoxyphenyl)-2-hydroxyethyl)acetamide;Acetamide, 2-chloro-N-(2-(2,5-dimethoxyphenyl)-2-hydroxyethyl)-;starbld0019185;UNII-VCL6EW672N;SCHEMBL6576604;DTXSID60463490;XAVXFUOLBMBEOC-UHFFFAOYSA-N

Chemical Property of 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Chemical Property:

• Boiling Point: 526.9±50.0 °C(Predicted)
• PSA: 71.28000
• Density: 1.250±0.06 g/cm3(Predicted)
• LogP: 1.93250
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 273.0767857
• Heavy Atom Count: 18
• Complexity: 265

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)OC)C(CNC(=O)CCl)O

Technology Process of 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

There total 6 articles about 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide 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: 50.0%

desglymidodrine (3600-87-1) + chloroacetyl chloride (79-04-9) → 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (60681-99-4)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; for 4h; Ambient temperature;

DOI:10.1021/jm00356a026

Reference yield:

2-bromo-2',5'-dimethoxyacetophenone (1204-21-3) → 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (60681-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / dioxane; H₂O / 1 h / Ambient temperature

2: KOH / diethyl ether; H₂O / 0.5 h / Heating

3: NH₃ / ethanol / 120 h / Ambient temperature

4: 50 percent / NaOH / CH₂Cl₂; H₂O / 4 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; ammonia; In 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jm00356a026

Reference yield:

1,2-epoxy-1-(2,5-dimethoxyphenyl)ethane (83436-65-1,141303-39-1) → 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (60681-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃ / ethanol / 120 h / Ambient temperature

2: 50 percent / NaOH / CH₂Cl₂; H₂O / 4 h / Ambient temperature

With sodium hydroxide; ammonia; In ethanol; dichloromethane; water;

DOI:10.1021/jm00356a026

upstream raw materials:

desglymidodrine

chloroacetyl chloride

2-bromo-2',5'-dimethoxyacetophenone

1,2-epoxy-1-(2,5-dimethoxyphenyl)ethane

Downstream raw materials:

6-(2,5-Dimethoxy-phenyl)-morpholin-3-one

C₁₂H₁₅⁽²⁾H₂NO₃

2-(2,5-dimethoxyphenyl)morpholine

Refernces

• 1、 -. "A process for the preparation of midodrine". Example 1. . Retrieved 2010/01/31.