2-(2-HYDROXYETHYL)-3-METHYL-1-OXO-1,5-DIHYDROPYRIDO[1,2-A]BENZIMIDAZOLE-4-CARBONITRILE

Base Information

• Chemical Name: 2-(2-HYDROXYETHYL)-3-METHYL-1-OXO-1,5-DIHYDROPYRIDO[1,2-A]BENZIMIDAZOLE-4-CARBONITRILE
• CAS No.: 166671-26-7
• Molecular Formula: C₁₅H₁₃N₃O₂
• Molecular Weight: 267.287
• Hs Code.: 2933990090
• Mol file: 166671-26-7.mol

Synonyms:NSC 649899

Chemical Property of 2-(2-HYDROXYETHYL)-3-METHYL-1-OXO-1,5-DIHYDROPYRIDO[1,2-A]BENZIMIDAZOLE-4-CARBONITRILE

Chemical Property:

• Vapor Pressure: 7.55E-09mmHg at 25°C
• Melting Point: 250 °C
• Refractive Index: 1.695
• Boiling Point: 449°Cat760mmHg
• Flash Point: 225.4°C
• PSA: 81.29000
• Density: 1.42g/cm³
• LogP: 1.49568

Purity/Quality:

98%min ^*data from raw suppliers

2-(2-HYDROXYETHYL)-3-METHYL-1-OXO-1,5-DIHYDROPYRIDO[1,2-A]BENZIMIDAZOLE-4-CARBONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S36/37:Wear suitable protective clothing and gloves.

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2-HYDROXYETHYL)-3-METHYL-1-OXO-1,5-DIHYDROPYRIDO[1,2-A]BENZIMIDAZOLE-4-CARBONITRILE

There total 1 articles about 2-(2-HYDROXYETHYL)-3-METHYL-1-OXO-1,5-DIHYDROPYRIDO[1,2-A]BENZIMIDAZOLE-4-CARBONITRILE 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: 90.0%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1) + 1H-benzimidazol-2-acetonitrile (4414-88-4) → 2-(2-hydroxyethyl)-3-methyl-1-xo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile (166671-26-7)

Guidance literature:

With ammonium acetate; at 130 - 140 ℃; for 1h;

DOI:10.1016/0223-5234(96)88241-9

Reference yield: 92.0%

2-(2-hydroxyethyl)-3-methyl-1-xo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile (166671-26-7) → 1-chloro-2-(2-chloroethyl)-3-methylpyrido<1,2-a>benzimidazole-4-carbonitrile (166671-24-5)

Guidance literature:

With trichlorophosphate; for 3h; Heating;

DOI:10.1016/0223-5234(96)88241-9

Reference yield:

2-(2-hydroxyethyl)-3-methyl-1-xo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile (166671-26-7) → 2,3-dihydro-4-methyl-1-(4-tolyl)-1H-pyrrolo<2,3-b>pyrido<1,2-a>benzimidazole-5-carbonitrile

Guidance literature:

Multi-step reaction with 3 steps

1: 87.5 percent / SOCl₂ / benzene / 2 h / Heating

2: 92 percent / POCl₃ / 3 h / Heating

3: 85.7 percent / dimethylformamide / 3 h / Heating

With thionyl chloride; trichlorophosphate; In N,N-dimethyl-formamide; benzene;

DOI:10.1016/0223-5234(96)88241-9

upstream raw materials:

3-acetyl-2-oxo-4,5-dihydrofuran

1H-benzimidazol-2-acetonitrile

Downstream raw materials:

1-chloro-2-(2-chloroethyl)-3-methylpyrido<1,2-a>benzimidazole-4-carbonitrile

1-(4-chlorophenyl)-2,3-dihydro-4-methyl-1H-pyrrolo<2,3-b>pyrido<1,2-a>benzimidazole-5-carbonitrile

2-(2-chloroethyl)-3-methyl-1-triphenylphosphoranylideneaminopyrido<1,2-a>benzimidazole-4-carbonitrile

3-methyl-2-(2-triphenylphosphoranylideneaminoethyl)-1-oxo-1H,5H-pyrido<1,2-a>benzymidazole-4-carbonitrile

Refernces

• 1、 Badawey, E.,Kappe, T.. "Benzimidazole condensed ring system. IX. Potential antineoplastics. New synthesis of some pyridobenzimidazoles and related derivatives". . p. 327 - 332. Retrieved 2007/10/02.