ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate

Base Information

• Chemical Name: ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate
• CAS No.: 75792-41-5
• Molecular Formula: C₁₁H₁₄N₂O₃
• Molecular Weight: 222.244
• Mol file: 75792-41-5.mol

Synonyms:ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate

Chemical Property of ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate

There total 1 articles about ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate 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: 70.0%

ethyl 4-carboxy-1,3,5-trimethylpyrrole-2-carboxylate (7473-16-7) → ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate (75792-41-5)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In acetonitrile; at 50 ℃; for 1.5h;

DOI:10.1021/jm00133a008

Reference yield:

ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate (75792-41-5) → N-<5-(benzyloxycarbonyl)-1,2,4-trimethylpyrrol-3-yl>-4-<<<4-<(tert-butyloxycarbonyl)amino>-1,3,5-trimethylpyrrol-2-yl>carbonyl>amino>-1,3,5-trimethylpyrrole-2-carboxamide (75792-57-3)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N / acetonitrile / 5 h / 50 °C

2: H₂ / 10percent Pd/C / methanol

3: 100 percent / Na / 4 h / 100 °C

5: H₂ / 10percent Pd/C / dioxane / 12 h

6: Et₃N, 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 0.25 h / 0 °C

7: 70 percent / glacial AcOH / dimethylformamide / 1.) 20 deg C, 2 d, 2.) 40 deg C, overnight

8: 100 percent / H₂ / 10percent Pd/C / dioxane; ethanol / 4 h / Heating

9: Et₃N, 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 0.25 h / 0 °C

10: 85 percent / glacial AcOH / dimethylformamide / 1.) 20 deg C, 48 h, 2.) 40 deg C, 24 h

With 2-chloro-1-methyl-pyridinium iodide; hydrogen; sodium; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00133a008

Reference yield:

ethyl 4-isocyanato-1,3,5-trimethylpyrrole-2-carboxylate (75792-41-5) → N-<5-(benzyloxycarbonyl)-1,2,4-trimethylpyrrol-3-yl>-4-<(tert-butyloxycarbonyl)amino>-1,3,5-trimethylpyrrole-2-carboxamide (75792-53-9)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / acetonitrile / 5 h / 50 °C

2: H₂ / 10percent Pd/C / methanol

3: 100 percent / Na / 4 h / 100 °C

5: H₂ / 10percent Pd/C / dioxane / 12 h

6: Et₃N, 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 0.25 h / 0 °C

7: 70 percent / glacial AcOH / dimethylformamide / 1.) 20 deg C, 2 d, 2.) 40 deg C, overnight

With 2-chloro-1-methyl-pyridinium iodide; hydrogen; sodium; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00133a008

upstream raw materials:

ethyl 4-carboxy-1,3,5-trimethylpyrrole-2-carboxylate

Downstream raw materials:

ethyl 4-<(benzyloxycarbonyl)amino>-1,3,5-trimethylpyrrole-2-carboxylate

benzyl 4-amino-1,3,5-trimethylpyrrole-2-carboxylate

4-<(tert-butyloxycarbonyl)amino>-1,3,5-trimethylpyrrole-2-carboxylic acid

benzyl 4-<(tert-butyloxycarbonyl)amino>-1,3,5-trimethylpyrrole-2-carboxylate

Refernces