4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

Base Information

• Chemical Name: 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile
• CAS No.: 1056737-14-4
• Molecular Formula: C₁₈H₁₇N₃O₄
• Molecular Weight: 339.351
• Mol file: 1056737-14-4.mol

Synonyms:4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

Chemical Property of 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

There total 5 articles about 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile 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: 84.0%

(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methyl 4-methylbenzenesulfonate (1056737-11-1) + sodium 4-cyanophenolate (3328-57-2) → 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile (1056737-14-4)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1021/jm8003448

Reference yield: 83.9%

(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methanol (1056737-05-3) + 4-cyanophenol (767-00-0) → 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile (1056737-14-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 48h; Reflux; Inert atmosphere;

DOI:10.1021/jm8003448

Reference yield:

5-Nitro-2-aminophenol (121-88-0) → 4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile (1056737-14-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium fluoride / N,N-dimethyl-formamide / 6 h / 60 °C

2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 20 °C

3: dimethylsulfide borane complex / tetrahydrofuran / Reflux

4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / Reflux

With potassium fluoride; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2011.06.089

upstream raw materials:

(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methanol

4-cyanophenol

(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methyl 4-methylbenzenesulfonate

sodium 4-cyanophenolate

Downstream raw materials:

4-[(7-amino-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

C₂₉H₃₃FN₄O₄

C₂₉H₃₂F₂N₄O₄

C₂₉H₃₂F₂N₄O₄