Methanesulfonamide → 5-Bromo-N-methanesulfonylpentanamide

HRID 1075845

Reaction equation

HRID 1075845 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12]>C(OCC)(=O)C>[CH3:1][S:2]([NH:5][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][Br:6])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 5211735-Bromovaleryl chloride

Product 1

HCID 202961415-Bromo-N-methanesulfonylpentanamideYield 74.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 23.5 g. (0.25 mole) of methanesulfonamide and 49.8 g. (0.25 mole) of 5-bromovaleric acid chloride was heated at 80-85° (oil bath) for 45 minutes. The brown reaction mixture was allowed to cool and was dissolved in ethyl acetate. The organic solution was washed with water and saturated brine, was dried (anhydrous magnesium sulfate), was Darcoed, concentrated, and cooled to afford the white, crystalline N-methanesulfonyl-5-bromovaleramide weighing 48.2 g. (74.8% yield) which melted at 97°-98°.

Workup

  1. additionA mixture of 23.5 g
  2. temperatureto cool
  3. washThe organic solution was washed with water and saturated brine
  4. dry with materialwas dried (anhydrous magnesium sulfate)
  5. concentrationconcentrated
  6. temperaturecooled

Sources & evidence

ORD record
ord-0eff3f6cdbf943e0a306fa9c72ffb88a
Source dataset
uspto-grants-1976_05
Patent number
US03954741

Linked notes

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