(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile

Base Information

• Chemical Name: (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile
• CAS No.: 634188-85-5
• Molecular Formula: C₂₄H₂₅N₃OS
• Molecular Weight: 403.548
• Mol file: 634188-85-5.mol

Synonyms:(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile

Chemical Property of (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile

There total 6 articles about (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile 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: 80.0%

5-iodovaleronitrile (6727-75-9) + (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione (28092-52-6) → (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile (634188-85-5)

Guidance literature:

5-iodovaleronitrile; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 30 ℃;

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione; nickel on carbon; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; at 20 ℃; for 30h;

DOI:10.1055/s-2003-41051

Reference yield:

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione (28092-62-8) → (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile (634188-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / potassium ethylthioxanthogenate / dimethylformamide / 3 h / 125 °C

2.1: Zn; TMSCl; 1,2-dibromoethane / tetrahydrofuran / 30 °C

2.2: 80 percent / 5 percent Ni/C / toluene; dimethylformamide; tetrahydrofuran / 30 h / 20 °C

With chloro-trimethyl-silane; potassium ethyltrithiocarbonate; ethylene dibromide; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; 2.2: Fukuyama coupling reaction;

DOI:10.1055/s-2003-41051

Reference yield:

benzylamine (100-46-9) → (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile (634188-85-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / 4 Angstroem molecular sieves / xylene / 12 h / Heating

2.1: 91 percent / polymer-supported-C₆H₄-4-SO₂-[(S)-2-CPh₂OH-pyrrolidin-1-yl]; BH₃*SMe₂ / tetrahydrofuran / 6 h / Heating

3.1: KBH₄; LiCl / tetrahydrofuran / 2 h / 20 °C

3.2: 90 percent / aq. HCl / tetrahydrofuran / 0.5 h / 55 °C

4.1: 93 percent / potassium ethylthioxanthogenate / dimethylformamide / 3 h / 125 °C

5.1: Zn; TMSCl; 1,2-dibromoethane / tetrahydrofuran / 30 °C

5.2: 80 percent / 5 percent Ni/C / toluene; dimethylformamide; tetrahydrofuran / 30 h / 20 °C

With chloro-trimethyl-silane; potassium borohydride; dimethylsulfide borane complex; 4 A molecular sieve; polymer-supported-C₆H₄-4-SO₂-[(S)-2-CPh₂OH-pyrrolidin-1-yl]; potassium ethyltrithiocarbonate; ethylene dibromide; lithium chloride; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; xylene; 5.2: Fukuyama coupling reaction;

DOI:10.1055/s-2003-41051

upstream raw materials:

5-iodovaleronitrile

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione

benzylamine

Downstream raw materials:

(3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile

biotin