3-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)benzonitrile

Base Information

• Chemical Name: 3-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)benzonitrile
• CAS No.: 304853-36-9
• Molecular Formula: C17H14 N2 O2
• Molecular Weight: 278.31
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50431103
• Wikidata: Q82244902
• Pharos Ligand ID: 8Y13X8AHLBUS
• ChEMBL ID: CHEMBL303209
• Mol file: 304853-36-9.mol

Synonyms:304853-36-9;3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)BENZONITRILE;CHEMBL303209;3-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-benzonitrile;SCHEMBL3872645;DTXSID50431103;HVXMMYUSBANZAI-UHFFFAOYSA-N;3-(4,4-dimethyl-2-oxo-1H-3,1-benzoxazin-6-yl)benzonitrile;BDBM50118695;3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo [d][1,3]oxazin-6-yl)-benzonitrile;3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo [d][1,3]oxazin-6-yl)benzonitrile;3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d] [1,3]oxazin-6-yl)-benzonitrile;3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)benzonitrile

Chemical Property of 3-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)benzonitrile

Chemical Property:

• Boiling Point: 409.0±45.0 °C(Predicted)
• PKA: 13.18±0.40(Predicted)
• PSA: 62.12000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 4.16048
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 278.105527694
• Heavy Atom Count: 21
• Complexity: 465

Purity/Quality:

97% ^*data from raw suppliers

3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)BENZONITRILE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C=CC(=C2)C3=CC=CC(=C3)C#N)NC(=O)O1)C

Technology Process of 3-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)benzonitrile

There total 3 articles about 3-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)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: 25.0%

3-cyanobromobenzene (6952-59-6) + (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (304853-90-5) → 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-3-yl)benzonitrile (304853-36-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; at 85 ℃; for 3h;

DOI:10.1021/jm025555e

Reference yield:

brofoxine (21440-97-1) → 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-3-yl)benzonitrile (304853-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

1.3: 81 percent / aq. hydrochloric acid / tetrahydrofuran; hexane / 20 °C

2.1: 25 percent / sodium carbonate; tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H₂O / 3 h / 85 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water;

DOI:10.1021/jm025555e

Reference yield:

2-(2-amino-5-bromophenyl)-propan-2-ol (304853-89-2) → 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-3-yl)benzonitrile (304853-36-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / tetrahydrofuran / 50 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: tetrahydrofuran; hexane / -78 - 20 °C

2.3: 81 percent / aq. hydrochloric acid / tetrahydrofuran; hexane / 20 °C

3.1: 25 percent / sodium carbonate; tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H₂O / 3 h / 85 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water;

DOI:10.1021/jm025555e

upstream raw materials:

3-cyanobromobenzene

(1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid

brofoxine

2-(2-amino-5-bromophenyl)-propan-2-ol

Downstream raw materials:

6-(3-Acetyl-phenyl)4,4-dimethyl-1,4-dihydro-benzo [d] [1,3]-oxazin-2-one

6-(3-Benzoyl-phenyl)4,4-dimethyl-1,4-dihydro-benzo[d] [1,3]-oxazin-2-one

Refernces

• 1、 -. "Cyclocarbamate derivatives as progesterone receptor modulators". . . Retrieved 2008/06/13.
• 2、 -. "Combination regimens using progesterone receptor modulators". . . Retrieved 2008/06/13.