6'-chloro-3'-methylspiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-trione

Base Information

• Chemical Name: 6'-chloro-3'-methylspiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-trione
• CAS No.: 107583-21-1
• Molecular Formula: C₁₁H₉ClN₄O₃
• Molecular Weight: 280.67
• Mol file: 107583-21-1.mol

Synonyms:Spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione,6'-chloro-3'-methyl-, (R)-

Chemical Property of 6'-chloro-3'-methylspiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-trione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 101.01000
• Density: 1.68g/cm³
• LogP: 0.11250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6'-chloro-3'-methylspiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-trione

There total 5 articles about 6'-chloro-3'-methylspiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-trione 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: 53.1%

2-ethylisothiourea hydrobromide (1071-37-0,133514-72-4) + 5-Chloro-1-methylcarbamoylisatin (107582-72-9) → dl-6-chloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (107582-74-1,107583-21-1)

Guidance literature:

With hydrogenchloride; triethylamine; In tetrahydrofuran;

Reference yield:

N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide (65798-06-3,17122-56-4) → dl-6-chloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (107582-74-1,107583-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. H₂SO₄ / Heating

2: 75 percent / Et₃N / dimethylformamide / 1 h / 0 °C

3: 1.) Et₃N, 2.) 10percent aq. HCl / 1.) THF, RT, 3 h, 2.) THF, 80 deg C, 3 h

With hydrogenchloride; sulfuric acid; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00089a021

Reference yield:

5-chloroindole 2,3-dione (17630-76-1) → dl-6-chloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (107582-74-1,107583-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / Et₃N / dimethylformamide / 1 h / 0 °C

2: 1.) Et₃N, 2.) 10percent aq. HCl / 1.) THF, RT, 3 h, 2.) THF, 80 deg C, 3 h

With hydrogenchloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00089a021

upstream raw materials:

2-ethylisothiourea hydrobromide

5-Chloro-1-methylcarbamoylisatin

N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide

5-chloroindole 2,3-dione

Refernces

• 1、 -. "Quinazolinone copmpounds useful for the prophyloxis and treatment of diabetic complications". . . Retrieved 2008/06/13.