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

HRID 245891Notes

Reaction equation

HRID 245891 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1/[CH:6]=[N:7]/[S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9].[CH3:14][Mg]Br>ClCCl>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH3:14]

Participants

4

Reactant 2

HCID 89421020(NE)-2-methyl-N-(1,3-oxazol-2-ylmethylidene)propane-2-sulfinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 712881642-Methyl-N-[1-(2-oxazolyl)ethyl]-2-propanesulfinamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, 2-methyl-propane-2-sulfinic acid 1-oxazol-2-yl-meth-(E)-ylideneamide (414 mg, 2.07 mmol) was dissolved in dichloromethane (7 ml). The reaction mixture was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether, 0.76 ml, 2.28 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 453 mg (96%) of 2-methyl-propane-2-sulfinic acid (1-oxazol-2-yl-ethyl)-amide as a 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-f0b93b702e7341c584f294165b9dc631
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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