Sodium Hydroxide → HCID 15389944, compound

HRID 1735840Notes

Reaction equation

HRID 1735840 reaction equation
[C:1]([NH:5][C:6](=[O:9])[C:7]#[CH:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Br:12]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[C:1]([NH:5][C:6](=[O:9])[C:7]#[C:8][Br:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 15389943HCID 15389943, compound

Product 1

HCID 15389944HCID 15389944, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.50 g of N-(tert-butyl)propiolamide was dissolved in 15 ml of methanol, to which 0.17 g of sodium hydroxide was added. 0.64 g of bromine was added dropwise to the mixture while stirring at a room temperature. 50 ml of 5%-aqueous solution of sodium thiosulfate was added to the reaction solution to extract with dichlormethane. The extracted solution was dried and concentrated. The residue was then purified by column chromatography (silica gel, eluent: ethyl acetate/hexane =1/5). Subsequently, 0.55 g of N-(tert-butyl)-3-bromopropiolamide was obtained by means of recrystallization from dichlormethane/hexane.

Workup

  1. additionwas added
  2. extractionto extract with dichlormethane
  3. customThe extracted solution was dried
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatography (silica gel, eluent: ethyl acetate/hexane =1/5)

Sources & evidence

ORD record
ord-748f91efe7b646a9a2c04fd43a5de563
Source dataset
uspto-grants-1996_07
Patent number
US05538998

Reaction notes

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