3-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-1,1-diethylurea

Base Information

• Chemical Name: 3-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-1,1-diethylurea
• CAS No.: 85045-98-3
• Molecular Formula: C16H23BrN2O4
• Molecular Weight: 387.274
• European Community (EC) Number: 641-761-4
• UNII: M6ZCM9M2TF
• Mol file: 85045-98-3.mol

Synonyms:85045-98-3;3-[3-ACETYL-4-(3-BROMO-2-HYDROXYPROPOXY)PHENYL]-1,1-DIETHYLUREA;N'-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-N,N-diethyl-urea;3-(3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl)-1,1-diethylurea;3-[3-Acetyl-4-[(2RS)-3-bromo-2-hydroxypropoxy]phenyl]-1,1-diethylurea (Bromhydrin Compound);Celiprolol Hydrochloride Imp. H (EP);Celiprolol Imp. H (EP);3-[3-Acetyl-4-[(2RS)-3-bromo-2-hydroxypropoxy]phenyl]-1,1-diethylurea;Bromhydrin Compound of Celiprolol;Celiprolol Hydrochloride Impurity H;Celiprolol Impurity H;M6ZCM9M2TF;SCHEMBL10567909;Celiprolol Hydrochloride Impurity H [EP Impurity];N'-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-N,N-diethylurea;N-[3-acetyl-4-[(2RS)-3-bromo-2-hydroxypropoxy]phenyl]-N',N'-diethylurea;Urea, N'-[3-acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-N,N-diethyl-

Chemical Property of 3-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-1,1-diethylurea

Chemical Property:

• Melting Point: 148-149.5℃
• PSA: 78.87000
• LogP: 2.97050
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 386.08412
• Heavy Atom Count: 23
• Complexity: 390

Purity/Quality:

99% ^*data from raw suppliers

N''-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-N,N-diethyl-urea ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)NC1=CC(=C(C=C1)OCC(CBr)O)C(=O)C
• Uses: N''-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-N,N-diethyl-urea is a derivative of Celiprolol (C254500, HCl salt) which is a cardioselective β1-adrenergic blocker.

Technology Process of 3-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-1,1-diethylurea

There total 4 articles about 3-[3-Acetyl-4-(3-bromo-2-hydroxypropoxy)phenyl]-1,1-diethylurea 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:

3-(4-Ethoxy-phenyl)-1,1-diethylharnstoff (1461-82-1) → 3-<3-Acetyl-4-(3-brom-2-hydroxy-propoxy)-phenyl>-1,1-diethylharnstoff (85045-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.4 percent / AlCl₃ / nitrobenzene / 4.5 h / 25 - 30 °C

2: 85 percent KOH / 4 h / 50 - 55 °C

3: 48 percent HBr / acetone; H₂O / 3 h

With potassium hydroxide; aluminium trichloride; hydrogen bromide; In water; nitrobenzene; acetone;

Reference yield:

N,N-diethylcarbamyl chloride (88-10-8) → 3-<3-Acetyl-4-(3-brom-2-hydroxy-propoxy)-phenyl>-1,1-diethylharnstoff (85045-98-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91.6 percent / KHCO₃ / acetone / 48 h / 20 - 30 °C

2: 93.4 percent / AlCl₃ / nitrobenzene / 4.5 h / 25 - 30 °C

3: 85 percent KOH / 4 h / 50 - 55 °C

4: 48 percent HBr / acetone; H₂O / 3 h

With potassium hydroxide; aluminium trichloride; hydrogen bromide; potassium hydrogencarbonate; In water; nitrobenzene; acetone;

Reference yield:

4-Ethoxyaniline (156-43-4) → 3-<3-Acetyl-4-(3-brom-2-hydroxy-propoxy)-phenyl>-1,1-diethylharnstoff (85045-98-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91.6 percent / KHCO₃ / acetone / 48 h / 20 - 30 °C

2: 93.4 percent / AlCl₃ / nitrobenzene / 4.5 h / 25 - 30 °C

3: 85 percent KOH / 4 h / 50 - 55 °C

4: 48 percent HBr / acetone; H₂O / 3 h

With potassium hydroxide; aluminium trichloride; hydrogen bromide; potassium hydrogencarbonate; In water; nitrobenzene; acetone;

upstream raw materials:

3-(4-Ethoxy-phenyl)-1,1-diethylharnstoff

N,N-diethylcarbamyl chloride

4-Ethoxyaniline

3-(3-Acetyl-4-hydroxy-phenyl)-1,1-diethylharnstoff

Downstream raw materials:

celiprolol

Refernces