Cesium carbonate → HCID 59761315, compound

HRID 1776176Notes

Reaction equation

HRID 1776176 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=O.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>C(#N)C.C(OCC)(=O)C>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:9]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH:1]=[CH:13][S:10]2(=[O:12])=[O:11])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 115793042-(Methylsulfonamido)benzaldehyde

Product 1

HCID 59761315HCID 59761315, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was synthesized according to the method described in WO 2008/073956 A2. To a solution of N-(2-formylphenyl)methanesulfonamide (2.0 g, 10 mmol) in anhydrous acetonitrile (45 mL) was added cesium carbonate (6.5 g, 20 mmol) and 4-methoxybenzylchloride (2.7 mL, 20 mmol). The mixture was heated to 50° C. and stirred for 48 hours, diluted with ethyl acetate, filtered through Celite, and concentrated. The crude product was purified by silica gel column chromatography (50-100% methylene chloride in hexanes) to give the product (0.9 g, 31%). 1H NMR (CDCl3, 300 MHz) δ 7.40-7.32 (m, 2H), 7.28-7.24 (m, 3H), 7.16-7.11 (m, 2H), 6.85-6.81 (m, 3H), 5.15 (s, 2H), 3.77 (s, 3H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel column chromatography (50-100% methylene chloride in hexanes)

Sources & evidence

ORD record
ord-a07ec44fc2394f198a1b8c2145e95fb6
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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