N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine

Base Information

• Chemical Name: N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine
• CAS No.: 1284258-88-3
• Molecular Formula: C₂₁H₁₉NO₂S
• Molecular Weight: 349.453
• Mol file: 1284258-88-3.mol

Synonyms:N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine

Chemical Property of N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine

There total 1 articles about N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine 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: 95.0%

para-methanesulfonylbenzaldehyde (5398-77-6) + Benzhydrylamine (91-00-9) → N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine (1284258-88-3)

Guidance literature:

In ethanol; for 3h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.09.052

Reference yield: 67.0%

diazoacetic acid ethyl ester (623-73-4) + N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine (1284258-88-3) → (2R,3R)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate + (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate (1284258-89-4)

Guidance literature:

N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine; With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane; In toluene; at 20 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

diazoacetic acid ethyl ester; In toluene; at -10 - 20 ℃; for 19h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.052

Reference yield:

N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine (1284258-88-3) → Florfenicol (73231-34-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane / toluene / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 19 h / -10 - 20 °C / Molecular sieve; Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran / 50 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

3.1: diethylamino-sulfur trifluoride; triethylamine / dichloromethane / 8 h / -40 - 20 °C / Inert atmosphere

4.1: water; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 6 h / 20 °C / 760.05 Torr

6.1: triethylamine / methanol / 3 h / Inert atmosphere; Reflux

With hydrogenchloride; lithium borohydride; diethylamino-sulfur trifluoride; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane; palladium 10% on activated carbon; water; hydrogen; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 1.1: Wulff aziridination / 1.2: Wulff aziridination / 3.1: Middleton fluorination;

DOI:10.1016/j.tet.2011.09.052

upstream raw materials:

para-methanesulfonylbenzaldehyde

Benzhydrylamine

Downstream raw materials:

(2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate

((2S,3S)-1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridin-2-yl)methanol

(2S,3S)-1-benzhydryl-2-(fluoromethyl)-3-(4-(methylsulfonyl)phenyl)aziridine

(1R,2S)-2-(benzhydrylamino)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propan-1-ol

Refernces