Methane → 5-Bromo-N-methanesulfonylpentanamide
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
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.950 g (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
- custom(ca. 5 minutes)
- temperatureto cool
- filtrationwas filtered
- additionwas diluted with hexane
- temperaturewith cooling
Sources & evidence
- ORD record
- ord-ccda27c2fe5c41eea6cfe8975ef8b3a8
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04244887
Reaction notes
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