Cesium carbonate → Methylenedioxybenzenesulfonamide 1-methyl-3,5-dimethylpyrazole

HRID 1253954Notes

Reaction equation

HRID 1253954 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:5]=[CH:6][CH:7]=2)[O:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:22][N:23]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24]1.C(OCC)(=O)C.CCCCCC>CN(C=O)C>[CH3:22][N:23]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24]1.[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([S:10]([NH2:13])(=[O:11])=[O:12])[CH:5]=[CH:6][CH:7]=2)[O:2]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 136927271-(chloromethyl)-3,5-dimethyl-1H-pyrazole hydrochlorideHCID 21226206Ethyl acetate hexaneHCID 224999261,3-Benzodioxole-4-sulfonamide

Product 1

HCID 66694438Methylenedioxybenzenesulfonamide 1-methyl-3,5-dimethylpyrazoleYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of Hoc methylenedioxybenzenesulfonamide free phenol (0.010 g, 0.020 mmol) in DMF (1 mL) was combined with anhydrous cesium carbonate (0.015 g, 0.047 mmol). Freshly prepared 1-chloromethyl-3,5-dimethylpyrazole hydrochloride (0.006 g, 0.033 mmol) in DMF (0.5 ml) was added dropwise. The solution was heated to 60° C. with stirring for 15 minutes, and was cooled and dried in vacuo to give a green oil. Flash column chromatography (1:1 ethyl acetate/hexane) gave Doc methylenedioxybenzenesulfonamide 1-methyl-3,5-dimethylpyrazole tethered product (0.002 g, 17%) as a colourless oil: Rf=0.25 (1:1 ethyl acetate/hexane); coupled LCMS showed the product as a single major peak with m/z 645 [M+H]+ at RT of 1.68 min.

Workup

  1. temperaturewas cooled
  2. customdried in vacuo
  3. customto give a green oil

Sources & evidence

ORD record
ord-72e0f8f28886456b952351a4e5bf08da
Source dataset
uspto-grants-2013_06
Patent number
US08455497B2

Reaction notes

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