Ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate

Base Information

• Chemical Name: Ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate
• CAS No.: 393802-93-2
• Molecular Formula: C16H17NO3S
• Molecular Weight: 303.37600
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50377017
• Nikkaji Number: J1.667.585G
• Wikidata: Q82166026
• Mol file: 393802-93-2.mol

Synonyms:ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate;393802-93-2;ethyl 4-acetyl-5-anilino-3-methylthiophene-2-carboxylate;ethyl 4-acetyl-3-methyl-5-(phenylamino)thiophene-2-carboxylate;DTXSID50377017;MFCD03414171;AKOS005069813;CS-0366818;1W-0238;J-520960;ethyl4-acetyl-3-methyl-5-(phenylamino)thiophene-2-carboxylate;3-Methyl-4-acetyl-5-anilinothiophene-2-carboxylic acid ethyl ester

Chemical Property of Ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate

Chemical Property:

• Melting Point: 123-124°C
• Boiling Point: 448.2±45.0 °C(Predicted)
• PKA: 1.10±0.38(Predicted)
• PSA: 83.64000
• Density: 1.227±0.06 g/cm3(Predicted)
• LogP: 4.25240
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 303.09291458
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=C(S1)NC2=CC=CC=C2)C(=O)C)C

Technology Process of Ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate

There total 4 articles about Ethyl 4-acetyl-5-anilino-3-methyl-2-thiophenecarboxylate 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: 79.0%

ethyl 2-sulfanylacetate (623-51-8) + 2-acetyl-3-hydroxy-N-phenyl-but-2-enimidothioic acid methyl ester → 4-acetyl-3-methyl-5-phenylamino-thiophene-2-carboxylic acid ethyl ester (393802-93-2)

Guidance literature:

With potassium carbonate; In ethanol;

DOI:10.1016/S0040-4039(01)02130-X

Reference yield: 47.0%

phenyl isothiocyanate (103-72-0) + ethyl bromoacetate (105-36-2) + acetylacetone (123-54-6,81235-32-7) → 4-acetyl-3-methyl-5-phenylamino-thiophene-2-carboxylic acid ethyl ester (393802-93-2)

Guidance literature:

acetylacetone; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

phenyl isothiocyanate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

ethyl bromoacetate; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1055/s-2001-18092

Reference yield:

phenyl isothiocyanate (103-72-0) → 4-acetyl-3-methyl-5-phenylamino-thiophene-2-carboxylic acid ethyl ester (393802-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: K₂CO₃ / dimethylformamide / 1 h / 20 °C

1.2: dimethylformamide / 2 h / 20 °C

1.3: 96 percent / dimethylformamide / 4 h / 20 °C

2.1: 79 percent / K₂CO₃ / ethanol / 6 h / Heating

With potassium carbonate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)00054-1

upstream raw materials:

phenyl isothiocyanate

ethyl bromoacetate

acetylacetone

ethyl 2-sulfanylacetate

Refernces

• 1、 Sommen, Geoffroy,Comel, Alain,Kirsch, Gilbert. "An improved method for the synthesis of aminothiophenes precursors of thieno[2,3-b]pyrrole". . p. 257 - 259. Retrieved 2007/10/03.