rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Base Information

• Chemical Name: rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile
• CAS No.: 444728-11-4
• Molecular Formula: C15H13ClN2S
• Molecular Weight: 288.801
• DSSTox Substance ID: DTXSID40463852
• Mol file: 444728-11-4.mol

Synonyms:444728-11-4;rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile;(+/-)-rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile;2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile;Clopidogrel Impurity K;JFDVAYOTONCKQN-UHFFFAOYSA-N;SCHEMBL889300;DTXSID40463852;BCP34205;AKOS030255495;FT-0664899;(2-Chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetonitrile;2-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl) acetonitrile;(+/-)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl) acetonitrile;(+/-)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetonitrile;(+/-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl) acetonitrile;(+/-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetonitrile;(+/-)-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetonitrile;2(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4h)yl)acetonitrile;alpha -(2-Chlorophenyl)-6,7-dihydro-thieno[3,2-c]pyridine-5(4H)-acetonitrile

Chemical Property of rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Chemical Property:

• Vapor Pressure: 6.46E-07mmHg at 25°C
• Melting Point: 125-127°C
• Boiling Point: 409.5oC at 760 mmHg
• PKA: 2.58±0.20(Predicted)
• Flash Point: 201.5oC
• PSA: 55.27000
• Density: 1.326g/cm3
• LogP: 3.96238
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 288.0487973
• Heavy Atom Count: 19
• Complexity: 366

Purity/Quality:

99% ^*data from raw suppliers

rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC2=C1SC=C2)C(C#N)C3=CC=CC=C3Cl
• Uses: A intermediate in the synthesis of the metabolite of the drug Clopidogrel An intermediate in the synthesis of the metabolite of the drug Clopidogrel.

Technology Process of rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

There total 11 articles about rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile 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: 90.3%

→ 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetonitrile (444728-11-4)

Guidance literature:

Product distribution / selectivity;

Reference yield: 87.4%

sodium cyanide (143-33-9,25596-52-5) + 2-chloro-benzaldehyde (89-98-5) + 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) → 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetonitrile (444728-11-4)

Guidance literature:

sodium cyanide; 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride; In methanol; water; for 0.666667h;

2-chloro-benzaldehyde; In methanol; water; at 23 - 50 ℃; for 6h;

With sodium metabisulfite; In methanol; water; at 25 - 30 ℃; for 2h;

Reference yield: 86.0%

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) + (+/-)-α-chloro-(2-chlorophenyl)-acetonitrile (5829-89-0) → 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetonitrile (444728-11-4)

Guidance literature:

With sodium hydrogencarbonate; In butan-1-ol; for 3h; Product distribution / selectivity; Heating / reflux;

upstream raw materials:

4,5,6,7-tetrahydrothieno[3,2-c]pyridine

2-chloro-benzaldehyde

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride

(+/-)-α-chloro-(2-chlorophenyl)-acetonitrile

Downstream raw materials:

(+/-)-(2-chlorophenyl)-(4,5,6,7-4H-thieno[3,2,-c]pyrid-5-yl) potassium acetate

sodium (+/-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)-acetate

clopidogrel

(S)-(+)-clopidogrel

Refernces

• 1、 Fuentes de Arriba, ángel L.,Lenci, Elena,Sonawane, Mahendra,Formery, Odilon,Dixon, Darren J.. "Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation". supporting information. p. 3655 - 3659. Retrieved 2017/03/21.
• 2、 -. "COMPOSITIONS AND METHODS FOR THE TREATMENT OF ATHEROTHROMBOSIS". . . Retrieved 2013/03/26.