Sodium hydride → N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

HRID 1899623Notes

Reaction equation

HRID 1899623 reaction equation
[CH3:1][C:2]1[C:3]([CH3:17])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[S:12][C:13]([Br:16])=[CH:14][CH:15]=1)(=[O:10])=[O:9].[H-].[Na+].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl>C1COCC1>[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][N:7]([C:6]1[O:5][N:4]=[C:3]([CH3:17])[C:2]=1[CH3:1])[S:8]([C:11]1[S:12][C:13]([Br:16])=[CH:14][CH:15]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 3857718N-(3,4-Dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

Product 1

HCID 23359448N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamideYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(4-Methyl-3-methyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide (680 mg, 2 mmol) in dry THF (2 ml) was added to sodium hydride (121 mg of a 60% oil dispersion, 3 mmol) in dry THF (1 ml). The resulting suspension was cooled to 0° C. and methoxy ethoxymethyl chloride (334 mg, 2.68 mmol) was added dropwise via syringe. The solution was warmed to room temperature, and stirring continued overnight. Evaporation of solvent left an oil that was extracted into ethyl acetate, washed with brine, dried over magnesium sulfate and evaporated. Flash chromatography of the residue on silica gel using 10-15% ethylacetate/hexanes yielded 480 mg (56%) of a colorless oil.

Workup

  1. temperatureThe solution was warmed to room temperature
  2. customEvaporation of solvent
  3. waitleft an oil that
  4. extractionwas extracted into ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6bcb7d7f45254986afd069b7f62ea811
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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