Dimethylformamide → HCID 58941235, compound

HRID 747612Notes

Reaction equation

HRID 747612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2OC)(=[O:11])=[O:10])=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[CH:3]=1.[H-].[Na+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].CN([CH:40]=[O:41])C>C(OCC)(=O)C>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:41][CH3:40])[CH:13]=1)(=[O:10])=[O:11])[CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 68567505HCID 68567505, compound

Product 1

HCID 58941235HCID 58941235, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 0.525 g of N-[4-chloro-2-(2-chlorobenzyl)phenyl]-2-methoxybenzenesulfonamide dissolved in 6 ml of DMF is added, at 0° C., 0.065 g of sodium hydride, after 40 minutes at this temperature 0.14 ml of ethyl 2-bromoacetate is introduced, and the mixture is left at room temperature for 18 hours. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) cyclohexane/ethyl acetate solvent mixture to give 0.272 g of the expected product, in the form of an oil.

Workup

  1. additionis added, at 0° C.
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a 90/10 (v/v) cyclohexane/ethyl acetate solvent mixture

Sources & evidence

ORD record
ord-cb5058d6ed0c4a8e8d11f92da47b47a6
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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