N-(3-formylphenyl)methanesulfonamide → [3-(Hydroxyethyl)phenyl](methylsulfonyl)amine

HRID 714466Notes

Reaction equation

HRID 714466 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)=[O:2].[CH3:14][Mg]Br>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:4]=[C:5]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)[CH3:14]

Participants

4

Reactant 2

HCID 2794787N-(3-formylphenyl)methanesulfonamideHCID 178418573HCID 178418573, compound

Product 1

HCID 43508614[3-(Hydroxyethyl)phenyl](methylsulfonyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon and at 0° C., 83 mg (0.417 mmol) of N-(3-formylphenyl)methanesulfonamide (Example 86A) were initially charged in 1 ml of abs. tetrahydrofuran. At 0° C., 99 mg (0.833 mmol) of methylmagnesium bromide (3 M in diethyl ether) were added dropwise (resulting in the formulation of a precipitate), and the reaction solution was stirred at this temperature for 2 h. The reaction solution was quenched with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated.

Workup

  1. customresulting in the formulation of a precipitate), and the reaction solution
  2. customThe reaction solution was quenched with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9ebb46efaf6049d5b841395a69ffd1af
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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