Burgess reagent

Burgess reagent
Names
	IUPAC name 1-Methoxy-N-triethylammoniosulfonyl-methanimidate
Identifiers
CAS Number	29684-56-8 ;
3D model ( JSmol)	Interactive image;
ChemSpider	2007108;
ECHA InfoCard	100.157.812
EC Number	629-648-8;
PubChem CID	2724994;
UNII	H5HBH02LFX ;
CompTox Dashboard (EPA)	DTXSID90894112 ;
	InChI InChI=1/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3 Key: YSHOWEKUVWPFNR-UHFFFAOYAN;
	SMILES O=S(=O)(N=C([O-])OC)[N+](CC)(CC)CC;
Properties
Chemical formula	C8H18N2O4S
Molar mass	238.30 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The Burgess reagent (methyl N-(triethylammoniumsulfonyl)carbamate) is a mild and selective dehydrating

Georgia Tech

.

The Burgess reagent is used to convert secondary and tertiary

inner salt

. A general mechanism is shown below.

Preparation

The reagent is prepared from

chlorosulfonylisocyanate by reaction with methanol and triethylamine in benzene:^[3]

References

doi:10.1021/ja01019a052
.

^ Sachin Khapli, Satyajit Dey & Dipakranjan Mal (2001). "Burgess reagent in organic synthesis" (PDF). J. Indian Inst. Sci. 81: 461–476. Archived from the original (PDF) on 2004-03-02.

doi:10.1021/jo00941a006
.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Burgess_reagent&oldid=1191336952"

[1] :10.1021/ja01019a052
.

[2] Sachin Khapli, Satyajit Dey & Dipakranjan Mal (2001). "Burgess reagent in organic synthesis" (PDF). J. Indian Inst. Sci. 81: 461–476. Archived from the original (PDF) on 2004-03-02.

[3] :10.1021/jo00941a006
.

[3]