Water → Methyl 6-[2-(2-diethylaminoethoxy)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoate

HRID 2177810Notes

Reaction equation

HRID 2177810 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:27][CH3:28])=[C:8]([C:13]([CH2:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[OH:26])(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Br[CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41].O>CN(C=O)C.C(Cl)Cl>[CH2:38]([N:39]([CH2:42][CH3:43])[CH2:40][CH2:41][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([CH2:16][C:13]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:27][CH3:28])[C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[CH:15][CH:14]=1)(=[O:19])=[O:18])[CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 124407792-Bromo-N,N-diethylethylamine hydrochlorideHCID 67107650Methyl 3-(furan-3-yl)-6-(2-hydroxybenzenesulphonylmethyl)-2-methoxybenzoate2×

Product 1

HCID 67107687Methyl 6-[2-(2-diethylaminoethoxy)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-(furan-3-yl)-6-(2-hydroxybenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 137, 0.081 g), cesium carbonate (0.144 g) and N-(2-bromoethyl)-N,N,-diethylamine hydrochloride (0.058 g) in DMF (5 ml) was stirred at room temperature. On completion of the reaction, water and DCM were added and the organic layer was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and DCM (1:19) to give methyl 6-[2-(2-diethylaminoethoxy)benzenesulphonylmethyl]-3-(furan-3-yl)-2-methoxybenzoate (0.101 g) as a colourless oil.

Workup

  1. additionwere added
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and DCM (1:19)

Sources & evidence

ORD record
ord-e710107173ff436f9abad00d23f1ad7d
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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