Sodium hydride → HCID 69314280, compound

HRID 2117761Notes

Reaction equation

HRID 2117761 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C=O)C>[CH3:3][O:4][CH2:5][CH2:6][N:7]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1587718HCID 1587718, compoundHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 69314280HCID 69314280, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.2 g, 55 mmol), was added to a solution of N-(2-methoxyethyl)-4-iodobenzenesulphonamide (Method 4; 15.8 g, 46.3 mmol), in DMF (250 ml), under nitrogen at 0° C. and the mixture stirred for 1 hour. 2-Trimethylsilylethoxymethyl chloride (10 g, 60 mmol), was added and the mixture stirred overnight at ambient temperature. The volatiles were removed by evaporation and the residue dissolved in ether, washed with water and then brine, dried (Na2SO4), and the solvent evaporated to give the title compound (22.6 g, 74%). NMR: 0.2 (s, 9H), 0.89 (t, 2H), 3.30 (s, 3H), 3.40-3.36 (m, 2H), 3.59-3.43 (m, 2H), 4.82 (s, 2H), 7.60 (d, 2H), 7.84 (d, 2H).

Workup

  1. stirringthe mixture stirred overnight at ambient temperature
  2. customThe volatiles were removed by evaporation
  3. dissolutionthe residue dissolved in ether
  4. washwashed with water
  5. dry with materialbrine, dried (Na2SO4)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-34a2ed7c8b554ee686fdc630b5696825
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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