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Synthesis of N-Sulfenylimines from Disulfides and Primary Methanamines
Robert Kaw?cki ; JOC,2022,87(11):7514-7520. DOI: 10.1021/acs.joc.2c00415 PubMed ID: 35587955
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Abstract: N-Sulfenylimines (sulfenimines, thiooximes, N-alkylidenesulfenamides) were efficiently synthesized through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results. A wide range of amines were reacted with aryl and alkyldisulfides, resulting in the formation of sulfenimines in a yield of 44–99%.
Purchased from AmBeed: 3300-51-4 ; 104-86-9 ; 623-33-6 ; 3959-07-7 ; 27757-85-3 ; 100-32-3 ; 629-19-6 ; 91-00-9 ; 5335-87-5 ; 3731-51-9 ; 6850-57-3 ; 128-08-5 ; 103-19-5 ; 2393-23-9
CAS No. : | 623-33-6 | MDL No. : | MFCD00012871 |
Formula : | C4H10ClNO2 | Boiling Point : | - |
Linear Structure Formula : | H3NCH2CO2CH2CH3Cl | InChI Key : | TXTWXQXDMWILOF-UHFFFAOYSA-N |
M.W : | 139.58 | Pubchem ID : | 2723640 |
Synonyms : |
Glycine ethyl ester monohydrochloride
|
Chemical Name : | H-Gly-OEt.HCl |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With triethylamine In dichloromethane | Example 2 Ii; Compound 4 was prepared according to the Ref: J. Hetero. Chem. 1995, 32, 1693-1702. Then, it was reduced by NaBH4ZLiCl in ethanol solution. Further oxidation by Dess-Martin reagent gave the desired aldehyde 6 in 25 percent overall two-step yield. |