2-methyl-N-[(1E)-1,3-oxazol-4-ylmethylidene]propane-2-sulfinamide → 2-Methyl-N-[1-(4-oxazolyl)ethyl]-2-propanesulfinamide

HRID 245899Notes

Reaction equation

HRID 245899 reaction equation
[O:1]1[CH:5]=[C:4](/[CH:6]=[N:7]/[S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[N:3]=[CH:2]1.[CH3:14][Mg]Br>ClCCl>[O:1]1[CH:5]=[C:4]([CH:6]([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH3:14])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 894209892-methyl-N-[(1E)-1,3-oxazol-4-ylmethylidene]propane-2-sulfinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 712881692-Methyl-N-[1-(4-oxazolyl)ethyl]-2-propanesulfinamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, 2-methyl-propane-2-sulfinic acid 1-oxazol-4-yl-meth-(E)-ylideneamide (548 mg, 2.74 mmol) was dissolved in dichloromethane (9 ml). The reaction mixture was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether, 1.0 ml, 3.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1 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 588 mg of 2-methyl-propane-2-sulfinic acid (1-oxazol-4-yl-ethyl)-amide as a light yellow 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-13b41da8a37245f79b4fba01f6a77073
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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