Ethyl 3-amino-5-anilino-4-cyano-2-thiophenecarboxylate

Base Information

• Chemical Name: Ethyl 3-amino-5-anilino-4-cyano-2-thiophenecarboxylate
• CAS No.: 59615-90-6
• Molecular Formula: C14H13N3O2S
• Molecular Weight: 287.342
• DSSTox Substance ID: DTXSID101184478
• Nikkaji Number: J1.667.586E
• Mol file: 59615-90-6.mol

Synonyms:Oprea1_839320;ethyl 3-amino-5-anilino-4-cyano-2-thiophenecarboxylate;DTXSID101184478;59615-90-6;SR-01000531628;SR-01000531628-1;ethyl 3-amino-5-anilino-4-cyanothiophene-2-carboxylate;Ethyl 3-amino-4-cyano-5-(phenylamino)-2-thiophenecarboxylate

Chemical Property of Ethyl 3-amino-5-anilino-4-cyano-2-thiophenecarboxylate

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 287.07284784
• Heavy Atom Count: 20
• Complexity: 389

Purity/Quality:

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#N)N

Technology Process of Ethyl 3-amino-5-anilino-4-cyano-2-thiophenecarboxylate

There total 7 articles about Ethyl 3-amino-5-anilino-4-cyano-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: 64.0%

2-cyano-3-methylthio-3-phenylaminoacrylonitrile (17823-65-3) + ethyl 2-sulfanylacetate (623-51-8) → 3-amino-4-cyano-5-phenylamino-thiophene-2-carboxylic acid ethyl ester (59615-90-6)

Guidance literature:

With potassium carbonate; In ethanol;

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

Reference yield: 19.0%

phenyl isothiocyanate (103-72-0) + ethyl bromoacetate (105-36-2) + malononitrile (109-77-3) → 3-amino-4-cyano-5-phenylamino-thiophene-2-carboxylic acid ethyl ester (59615-90-6)

Guidance literature:

malononitrile; 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:

ethyl 2-bromoacetoacetate (84911-18-2,609-13-2) + potassium (2,2-dicyano-1-phenylaminoethen-1-yl)thiolate → 3-amino-4-cyano-5-phenylamino-thiophene-2-carboxylic acid ethyl ester (59615-90-6)

Guidance literature:

With ethanol; at 20 ℃; for 0.333333h; regioselective reaction; Green chemistry;

DOI:10.1016/j.tetlet.2013.11.014

upstream raw materials:

phenyl isothiocyanate

chloroacetic acid ethyl ester

malononitrile

ethyl bromoacetate

Downstream raw materials:

3,4-Diamino-6-phenyl-thieno<2,3-b>-pyrrol-2,5-dicarbonsaeurediethylester

3,4-Diamino-5-benzoyl-6-phenyl-thieno<2,3-b>-pyrrol-2-carbonsaeureethylester

6-Phenyl-4,7-dioxo-3,4,6,7-tetrahydro-pyrimido<4,5'-4,5>thieno<2,3-b>pyrimido<4,3-b>pyrrol

N-(7-cyano-2-methyl-4-oxo-4H-thieno[3,2-d][1,3]oxazin-6-yl)-N-phenylacetamide