1,3-Dibromopropane → HCID 13961622, compound

HRID 2051958Notes

Reaction equation

HRID 2051958 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.[O-]CC.[Na+].[Br:26][CH2:27][CH2:28][CH2:29]Br>C(O)C>[Br:26][CH2:27][CH2:28][CH2:29][N:9]([O:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][CH:20]=1)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 2723922Sodium ethoxideHCID 20185710HCID 20185710, compound

Product 1

HCID 13961622HCID 13961622, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

N-(p-methoxybenzyloxy)-p-toluenesulfonamide (61.4 g) was added to a solution of sodium ethoxide in absolute ethanol (Na:4.6 g, absolute C2H5OH:540 ml) and stirred at 70° C. for 1.5 hours. After cooling at ambient temperature, 1,3-dibromopropane (121.2 g) was added to the mixture, and then the mixture was refluxed with stirring for 2 hours and filtered. The filtrate was concentrated under reduced pressure. To the residue was added a mixture of ethyl acetate and water, and the organic layer was separated, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give an oil, which was crystallized from a mixture of ethyl acetate and n-hexane to give N-(3-bromopropyl)-N-(p-methoxybenzyloxy)-p-toluenesulfonamide (75.1 g).

Workup

  1. temperatureAfter cooling at ambient temperature
  2. temperaturethe mixture was refluxed
  3. stirringwith stirring for 2 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added
  7. additiona mixture of ethyl acetate and water
  8. customthe organic layer was separated
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to dryness under reduced pressure
  11. customto give an oil, which
  12. customwas crystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-20f8c872f0154ec7afc93155440bad6a
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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