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ChemicalBook CAS DataBase List Burgess reagent
29684-56-8

Burgess reagent synthesis

1synthesis methods
Methoxycarbonylsulfamoyl]triethylammonium hydroxide, inner salt is easily prepared in two simple steps from chlorosulfonyl isocyanate as shown in the following scheme. The white crystalline solid Burgess reagent (m.p : 71-72°C from toluene) is air and moisture sensitive and, as such, needs to be stored in the cold and under an inert atmosphere. Burgess reagent
-

Yield:29684-56-8 63%

Reaction Conditions:

in benzene at 20;

Steps:

Synthesis of Methyl(carboxysulfamoyl)triethylammonium Hydroxide 1

Methyl(carboxysulfamoyl)triethylammonium hydroxide 1 was prepared using the Organic Syntheses procedure published by Burgess et al.[2] Compound 1 was obtained as colourless crystals (mp 67.2-69.5 C, lit[2] mp 71-728C), yield 63 %. dH (600 MHz, CDCl3) 1.41 (9H, t, JHH 7.2, NCH2CH3), 3.47 (6H, q, JHH 7.2, NCH2CH3, 3.70 (3H, s, CH3), dC (151 MHz, CDCl3) 9.38 (NCH2CH3), 50.43 (NCH2CH3), 53.26 (OCH3), 158.2 (C=O). nmax (CHCl3)/cm_1 3020 (w), 2951 (w), 1698 (m), 1460 (w), 1438 (w), 1342 (w), 1262 (s), 1222 (w), 1202 (w), 1187 (w), 1110 (w), 1039 (w), 965 (w), 866 (w), 734 (w), 714 (w), 668 (w), 623 (w), 590 (w), 577 (w), 563 (w). nmax (solid)/cm_1 3046 (w), 2996 (w), 2979 (w), 2951 (w), 1719 (w), 1688 (m), 1455 (m), 1441 (m), 1402 (w), 1338 (w), 1326 (m), 1304 (w), 1241 (s), 1219 (m), 1186 (m), 1111 (m), 1092 (m), 1042 (m), 1023 (m), 960 (m), 893 (w), 856 (m), 835 (m), 787 (m), 717 (m), 695 (w), 679 (w), 668 (w), 651 (w), 641 (w), 627 (m), 600 (s), 577 (m).

References:

Arduengo, Anthony J.;Uchiyama, Yosuke;DIxon, David A.;Vasiliu, Monica [Australian Journal of Chemistry,2019,vol. 72,# 11,p. 867 - 873]

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