| Identification | Back Directory | [Name]
N-(chloracetyl)methanesulfonamide | [CAS]
202658-88-6 | [Synonyms]
N-(chloracetyl)methanesulfonamide
2-chloro-N-(methylsulfonyl)-Acetamide
Acetamide, 2-chloro-N-(methylsulfonyl)- | [EINECS(EC#)]
814-170-6 | [Molecular Formula]
C3H6ClNO3S | [MDL Number]
MFCD20637131 | [MOL File]
202658-88-6.mol | [Molecular Weight]
171.6 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
3.43±0.40(Predicted) | [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 Information | Back Directory | [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increased to 65 °C. The reaction temperature was then increased to 65 °C. After the dropwise addition, the ice bath was withdrawn, the temperature was gradually increased to 65 °C and the reaction was stirred at this temperature for 12 h. The reaction progress was monitored by TLC.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.
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