Sodium hydride → 2-Bromo-N-Methylsulfonylacetamide

HRID 53668Notes

Reaction equation

HRID 53668 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].[Br:8][CH2:9][C:10](Br)=[O:11]>O1CCCC1>[Br:8][CH2:9][C:10]([NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 61147Bromoacetyl bromideHCID 72879Methanesulfonamide

Product 1

HCID 2629442-Bromo-N-Methylsulfonylacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (1.68 g×60% ) was added to a stirred solution of methanesulfonamide (2.0 g) in dry tetrahydrofuran (20 ml) at room temperature. The resulting solution was stirred at room temperature for 1 hour, as which time it was treated with a solution of bromoacetyl bromide (4.2 g) in dry tetrahydrofuran (10 ml). After 1 hour the solvent was removed under reduced pressure and the residue taken up in water and acidified to pH3. The acidic solution was extracted into ethyl acetate, dried (MgSO4), filtered and the solvent removed under reduced pressure. Recrystallisation from isopropanol afforded the product as white needles: mp 112°-114° C.

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure
  2. extractionThe acidic solution was extracted into ethyl acetate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-575b933edd854cfcb80aab968d02232c
Source dataset
uspto-grants-1997_04
Patent number
US05620989

Reaction notes

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