N-(chloracetyl)methanesulfonamide

N-(chloracetyl)methanesulfonamide Property

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

N-(chloracetyl)methanesulfonamide Chemical Properties,Usage,Production

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increased to 65 °C. The reaction temperature was then increased to 65 °C. After the dropwise addition, the ice bath was withdrawn, the temperature was gradually increased to 65 °C and the reaction was stirred at this temperature for 12 h. The reaction progress was monitored by TLC.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.