N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetamidine

Base Information

• Chemical Name: N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetamidine
• CAS No.: 87605-40-1
• Molecular Formula: C₁₃H₁₄Cl₄N₂O₂S
• Molecular Weight: 404.144

Synonyms:N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetamidine

Chemical Property of N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetamidine

Chemical Property:

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Useful:

Technology Process of N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetamidine

There total 1 articles about N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetamidine 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: 82.0%

2,2,2-Trichloro-N-((3R,4S)-4-chloro-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-acetimidoyl chloride (87605-39-8) + benzylamine (100-46-9) → N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-acetamidine (87605-40-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 2.5h; Ambient temperature;

DOI:10.1246/cl.1983.1275

Reference yield: 85.0%

N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-acetamidine (87605-40-1) → (3aR,6aS)-1-Benzyl-2-trichloromethyl-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole 5,5-dioxide (87605-41-2)

Guidance literature:

With aluminum oxide; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1246/cl.1983.1275

Reference yield:

N-Benzyl-2,2,2-trichloro-N'-((3S,4R)-4-chloro-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-acetamidine (87605-40-1) → (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one (56198-34-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / basic alumina / acetonitrile / 2 h / Ambient temperature

2: 88 percent / 4 M NaOH / ethanol / 1.5 h / Heating

3: 86 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -40 - 25 °C

4: 68 percent / LiAlH₄ / diethyl ether / 7 h / -15 - -10 °C

With aluminum oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; acetonitrile;

DOI:10.1246/cl.1983.1275

upstream raw materials:

2,2,2-Trichloro-N-((3R,4S)-4-chloro-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-acetimidoyl chloride

benzylamine

Downstream raw materials:

(3aR,6aS)-1-Benzyl-2-trichloromethyl-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole 5,5-dioxide

(3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one

cis-N-benzylperhydrothieno<3,4-d>imidazole-2-one 5,5-dioxide

(3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one 5,5-dioxide

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