HCID 89421012, compound → N-[1-(3-Isoxazolyl)ethyl]-2-methyl-2-propanesulfinamide

HRID 245904Notes

Reaction equation

HRID 245904 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[N:7]/[S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[N:2]1.[CH3:14][Mg]Br>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH3:14])=[N:2]1

Participants

4

Reactant 2

HCID 89421012HCID 89421012, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71288179N-[1-(3-Isoxazolyl)ethyl]-2-methyl-2-propanesulfinamideYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, 2-methyl-propane-2-sulfinic acid 1-isoxazol-3-yl-meth-(E)-ylideneamide (584 mg, 2.92 mmol) was dissolved in dichloromethane (10 ml). The reaction mixture was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether, 1.1 ml, 3.3 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 h then quenched with saturated aqueous NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to afford 655 mg of 2-methyl-propane-2-sulfinic acid (1-isoxazol-3-yl-ethyl)-amide as a colorless oil.

Workup

  1. customthen quenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-851eae167f8646ffb61435303adbfd16
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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