Ethanol → 6-(4-Chloro-phenylsulfanyl)-hexylamine

HRID 2097362Notes

Reaction equation

HRID 2097362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C2C=CC=C3C(NC(=O)C=23)=O)=[CH:4][CH:3]=1.O.[NH2:27]N.CCO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:27])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 866225746-(4-Chlorophenylsulfanyl)-hexylphthalimide

Product 1

HCID 231324146-(4-Chloro-phenylsulfanyl)-hexylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[6-(4-Chloro-phenylsulfanyl)-hexylphthalimide (7.47 g, 20 mmol) and hydrazine hydrate (6.1 ml, 100 mmol) were dissolved in THF (50 mL) and EtOH (50 mL) and stirred under reflux for 17 h. The solvent was removed under reduced pressure, the residue was suspended in THF (100 mL) and the precipitate was filtered off, washed with THF (1×50 mL) and the filtrate was concentrated under reduced pressure. The residue was resuspended in THF (25 mL), the precipitate was filtered off and the filtrate was concentrated to give the title compound.

Workup

  1. temperatureunder reflux for 17 h
  2. customThe solvent was removed under reduced pressure
  3. filtrationthe precipitate was filtered off
  4. washwashed with THF (1×50 mL)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. filtrationthe precipitate was filtered off
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e9eeef1cc87e45759d828a2ceddda0c9
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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