Hydrochloric Acid → 1156914-56-5

HRID 870119Notes

Reaction equation

HRID 870119 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)=[CH:4][CH:3]=1.O.NN.Cl>C(O)C.ClCCl>[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 58473571HCID 58473571, compound

Product 1

HCID 435310881156914-56-5Yield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

N(4-(4-bromophenoxy)butyl)phthalimide (6.01 g, 16.1 mmol) is dissolved in ethanol (200 mL) under nitrogen, followed by the addition of hydrazine monohydrate (7.8 mL, 161 mmol). The reaction was refluxed at 80° C. for 2 hours. Once reaction completed (solids formed at the top layer), cooled reaction to room temperature and neutralized with 1M HCl (50 mL). The mixture is allowed to stir until all solids are completely dissolved and diluted with dichloromethane (150 mL). The solution was extracted with two portions of saturated NaHCO3 (2×). The organic layers were combined, washed with brine and water, then dried over MgSO4, and filtered. Removal of solvent yields a yellow oil (2.93 g, 75%).

Workup

  1. customOnce reaction
  2. customformed at the top layer),
  3. temperaturecooled
  4. customreaction to room temperature
  5. dissolutionare completely dissolved
  6. extractionThe solution was extracted with two portions of saturated NaHCO3 (2×)
  7. washwashed with brine and water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customRemoval of solvent

Sources & evidence

ORD record
ord-434b93d8db8b4ef8a0cadfad4b5702c9
Source dataset
uspto-grants-2015_03
Patent number
US08969509B2

Reaction notes

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