Methane → 5-Bromo-N-methanesulfonylpentanamide

HRID 371767

Reaction equation

HRID 371767 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>C(Cl)Cl>[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

5

Reactant 3

HCID 297MethaneHCID 72879MethanesulfonamideHCID 5211735-Bromovaleryl chloride

Product 1

HCID 202961415-Bromo-N-methanesulfonylpentanamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.950g (0.01 mole) of methanesulfonamide and 1.80 g. (0.01 mole) of 5-bromovaleric acid chloride was heated on a steam bath until gas evolution ceased (ca. 5 minutes). The brown reaction mixture was allowed to cool and was dissolved in methylene chloride. The methylene chloride solution was treated with Darco, was filtered, and was diluted with hexane with cooling to afford the white, crystalline N-methanesulfonyl-5-bromovaleramide weighing 2.22 g. (86.0% yield) which melted at 88°-89°.

Workup

  1. custom(ca. 5 minutes)
  2. temperatureto cool
  3. filtrationwas filtered
  4. additionwas diluted with hexane
  5. temperaturewith cooling

Sources & evidence

ORD record
ord-6fe8181ee96f41b8a0150e58aa944655
Source dataset
uspto-grants-1978_05
Patent number
US04087604

Linked notes

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