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

HRID 990040Notes

Reaction equation

HRID 990040 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[S:13][C:14]([Br:17])=[CH:15][CH:16]=2)(=[O:11])=[O:10])[O:4][N:3]=1.[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:8]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[C:6]=1[CH3:7])[S:9]([C:12]1[S:13][C:14]([Br:17])=[CH:15][CH:16]=1)(=[O:10])=[O:11]

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-(3,4-Dimethyl-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 methoxyethoxymethyl 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% ethyl acetate/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-2dca824bc65a463581cf2a0941263579
Source dataset
uspto-grants-2002_10
Patent number
US06458805B2

Reaction notes

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