(S,E)-N-benzylidene-tert-butylsulfinamide

Base Information

• Chemical Name: (S,E)-N-benzylidene-tert-butylsulfinamide
• CAS No.: 186249-74-1
• Molecular Formula: C₁₁H₁₅NOS
• Molecular Weight: 209.312
• Mol file: 186249-74-1.mol

Synonyms:(S,E)-N-benzylidene-tert-butylsulfinamide

Chemical Property of (S,E)-N-benzylidene-tert-butylsulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S,E)-N-benzylidene-tert-butylsulfinamide

There total 5 articles about (S,E)-N-benzylidene-tert-butylsulfinamide 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: 96.0%

S-tert-butylsulfinimide (146374-27-8) + benzaldehyde (100-52-7) → (S,E)-N-benzylidene-tert-butylsulfinamide (186249-74-1)

Guidance literature:

With pyridinium p-toluenesulfonate; magnesium sulfate; In dichloromethane; at 20 ℃; for 24h;

Reference yield: 95.0%

benzaldehyde (100-52-7) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S,E)-N-benzylidene-tert-butylsulfinamide (186249-74-1)

Guidance literature:

With copper(II) sulfate; In dichloromethane; for 24h; Inert atmosphere;

DOI:10.1080/00397910802654898

Reference yield: 20.0%

(2R,4S)-3-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-1,2,3-oxathiazolidine 2-oxide (1279696-96-6) + tert-butylmagnesium chloride (677-22-5) + benzaldehyde (100-52-7) → (S,E)-N-benzylidene-tert-butylsulfinamide (186249-74-1)

Guidance literature:

(2R,4S)-3-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-1,2,3-oxathiazolidine 2-oxide; tert-butylmagnesium chloride; In tetrahydrofuran; at -78 ℃; Inert atmosphere; Cooling with acetone-dry ice;

With lithium hexamethyldisilazane; In tetrahydrofuran; at -68 - 20 ℃; Inert atmosphere;

benzaldehyde; With titanium(IV) tetraethanolate; In tetrahydrofuran; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201003222

upstream raw materials:

tert-butylsulfinyl chloride

benzaldehyde

(S)-2-methylpropane-2-sulfinamide

(2R,4S)-3-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-1,2,3-oxathiazolidine 2-oxide

Downstream raw materials:

N-methoxy-N-methyl-3-(2-methyl-propane-2-sulfinylamino)-3-phenyl-propionamide

(S)-2-methylpropane-2-sulfinic acid [(R)-phenyl-p-tolylmethyl]amide

tert-butyl 1-((R)-((S)-1,1-dimethylethyl-sulfinamido)(phenyl)methyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate