Cesium carbonate → Methyl 4-(6-quinaldinyloxy)-3-methylsulfonyl-benzoate

HRID 1684560Notes

Reaction equation

HRID 1684560 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.Cl[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[S:24]([CH3:27])(=[O:26])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C)C(=O)N(C)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=3[S:24]([CH3:27])(=[O:25])=[O:26])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:12]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 5943956-Hydroxy-2-methylquinolineHCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

Product 1

HCID 67715635Methyl 4-(6-quinaldinyloxy)-3-methylsulfonyl-benzoateYield 85.4%

Reagents, catalysts & solvents 1

HCID 12437TetramethylureaSolvent

Procedure

2 g of 6-hydroxyquinaldine, 3.12 g of methyl 4-chloro-3-methylsulfonyl-benzoate and 12.28 g of Cs2CO3 are stirred in 50 ml of anhydrous tetramethylurea at 110° C. for 1 h. The mixture is cooled, 250 ml of saturated aqueous NaHCO3 solution are added and extraction is carried out 3 times with 125 ml of EA. The extracts are dried over Na2SO4, the solvent is removed in vacuo and the residue is chromatographed with MTB. 3.98 g of a colorless foam are obtained. Rf (MTB)=0.31 MS (ES): 372 (M+H)+

Workup

  1. temperatureThe mixture is cooled
  2. extractionextraction
  3. dry with materialThe extracts are dried over Na2SO4
  4. customthe solvent is removed in vacuo
  5. customthe residue is chromatographed with MTB

Sources & evidence

ORD record
ord-68c3d2c20f4043c88fa17be9786cd7ed
Source dataset
uspto-grants-1997_06
Patent number
US05641792

Reaction notes

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