Acetone → HCID 178454375, compound

HRID 1815539Notes

Reaction equation

HRID 1815539 reaction equation
C([CH:8]1[O:16][C:15]2[C:10](=[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:12]=[CH:13][CH:14]=2)[O:9]1)(OC(C)(C)C)=O.[C:21](=[O:24])([O-])[O-:22].[Cs+].[Cs+].ClCC[N:30]1[CH:34]=[CH:33][CH:32]=[N:31]1.[I-].[Na+].[CH3:37]C(C)=O>C(OCC)(=O)C.CCCCCC>[CH2:11]([C:12]1[CH:13]=[CH:14][NH:31][N:30]=1)[CH3:10].[CH2:8]1[O:16][C:15]2[C:10](=[C:11]([S:17]([NH:20][C:21]([O:22][C:33]([CH3:34])([CH3:37])[CH3:32])=[O:24])(=[O:18])=[O:19])[CH:12]=[CH:13][CH:14]=2)[O:9]1

Participants

7

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 6422141-(2-Chloroethyl)-1H-pyrazoleHCID 86593015Boc methylenedioxybenzenesulfonamide

Product 1

HCID 178454375HCID 178454375, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
55 °C

Procedure

A solution of Boc methylenedioxybenzenesulfonamide free phenol (0.010 g, 0.020 mmol) in acetone (1 mL) was combined with cesium carbonate (0.015 g, 0.047 mmol), 1-(2-chloroethyl)pyrazole (0.004 g, 0.031 mmol) and sodium iodide (˜1 mg, 0.007 mmol). The solution was heated to 55° C. with stirring for 60 hours, and was cooled and dried in vacuo to give a yellow oil. Flash column chromatography (1:3 ethyl acetate/hexane) gave Boc methylenedioxybenzenesulfonamide ethylpyrazole tethered product (0.0015 g, 13%) as a colourless oil: Rf=0.20 (1:1 ethyl acetate/hexane); coupled LCMS showed the product as a single major peak with m/z 631 [M+H]+ at RT of 1.65 min.

Workup

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

Sources & evidence

ORD record
ord-8951edee767640b2b76bd46cac924eb6
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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