Sodium hydride → HCID 68828788, compound

HRID 2100377Notes

Reaction equation

HRID 2100377 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].I[CH2:14][CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:14][CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6425184Methyl 4-Bromo-3-hydroxybenzoateHCID 21344428N-(2-Iodoethyl)methanesulfonamide

Product 1

HCID 68828788HCID 68828788, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-bromo-3-hydroxybenzoate (231 mg) and N-(2-iodoethyl)methanesulfonamide (274 mg) were dissolved in DMF (10 ml), sodium hydride (64 mg, 60% dispersion in mineral oil) was added and the reaction heated at 80° C. for 20 hours. The solvent was evaporated in vacuo and the residue purified by SPE (5 g, Si), eluting with a chloroform/methanol gradient (0-5% methanol). The solvents were evaporated under vacuum from the product fractions to give methyl 4-bromo-3({2-[(methylsulfonyl)amino]ethyl}oxy)benzoate as a colourless gel (83 mg).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified by SPE (5 g, Si)
  3. washeluting with a chloroform/methanol gradient (0-5% methanol)
  4. customThe solvents were evaporated under vacuum from the product fractions

Sources & evidence

ORD record
ord-acaa5b19ac3749a6b58fd89515c585b1
Source dataset
uspto-grants-2009_08
Patent number
US07572790B2

Reaction notes

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