Methanesulfonamide → 5-Bromo-N-methanesulfonylpentanamide

HRID 561772

Reaction equation

HRID 561772 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>[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:12]

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 5211735-Bromovaleryl chloride

Product 1

HCID 202961415-Bromo-N-methanesulfonylpentanamideYield 88.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture consisting of methanesulfonamide (4.76 g) and 5-bromovaleric acid chloride (10 g) was heated at 85-90° C. for one hour, was cooled to room temperature, and was diluted with ethyl acetate (75 mL). The solution was washed with water, brine, and dried over sodium sulfate. The solution was filtered and evaporated to 40 mL of solvent, then cooled to −15° C. A white precipitate formed, which was collected by filtration to afford the title intermediate (11.4 g, 88%) as a white solid; melting point 98-100° C.

Workup

  1. temperaturewas cooled to room temperature
  2. washThe solution was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. customevaporated to 40 mL of solvent
  6. temperaturecooled to −15° C
  7. customA white precipitate formed
  8. filtrationwhich was collected by filtration

Sources & evidence

ORD record
ord-4ccd0fc749d9494d93f44d84999ebb6f
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Linked notes

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