N-(chloracetyl)methanesulfonamide Chemical Properties

Melting point:

114 - 116°C

Density 

1.474±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.43±0.40(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C3H6ClNO3S/c1-9(7,8)5-3(6)2-4/h2H2,1H3,(H,5,6)

InChIKey

BKLFBPWLPOUGTM-UHFFFAOYSA-N

SMILES

C(NS(C)(=O)=O)(=O)CCl

N-(chloracetyl)methanesulfonamide Usage And Synthesis

Uses

2-Chloro-N-(methylsulfonyl)acetamide acts as a reagent for the preparation of piperazinylquinolonecarboxamides as antivirals. Solid phase preparation of peptidines, glycine-amidine-based oligomers.

Synthesis

To a 2-liter three-necked flask was added 1 liter of ethyl acetate and 66 g (0.69 mol) of methanesulfonamide and dissolved with stirring. Under cooling in an ice bath, 109 g (0.77 mol) of chloroacetyl chloride was slowly added dropwise, with the rate of the drop being controlled to maintain the reaction temperature at no more than 65 °C. The reaction temperature was then increased to 65 °C. The reaction temperature was then increased to 65 °C. After the dropwise addition, the ice bath was withdrawn, the temperature was gradually increased to 65 °C and the reaction was stirred at this temperature for 12 h. The reaction progress was monitored by TLC. After completion of the reaction, the reaction mixture was slowly cooled to 0 °C and a large amount of white solid was precipitated. The solid was collected by filtration, washed with cold ethyl acetate and dried under vacuum to afford 112 g of 2-chloro-N-(methylsulfonyl)acetamide (SLP-10b, X = Cl) in 94% yield. Product characterization: 1H NMR (400 MHz, CDCl3) δ: 4.02 (s, 2H), 3.28 (s, 3H); ESI/MS m/z: 171 [M+H]+.

storage

Inert atmosphere,Store in freezer, under -20℃.

References

N-(chloracetyl)methanesulfonamide is prepared by the reaction of methanesulfonamide and chloroacetyl chloride. The specific synthesis steps are as follows:
In a 2-liter reaction flask, 1 liter of ethyl acetate and 66 grams of methylsulfonamide were added, and 109 grams of chloroacetyl chloride was gradually added; the temperature was gradually increased to 65C for 12 hours until the end of the reaction.The reaction solution gradually cooled to 0 degree, and a large amount of white solid precipitated; it was filtered and dried to obtain 112 g of solid SLP-10b (X=Cl).Yield: 94%.H NMR (400MHz, CDCl3): delta 4.02 (s, 2H), 3.28s, 3H)ESI/MS+(m/z):171.