Water → Phenyl-2-aminoethyl sulfide

HRID 915660Notes

Reaction equation

HRID 915660 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[H-].[Na+].Cl[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11]N=1.O.O1CCOC[CH2:17]1>C(Cl)Cl>[C:11]1([S:5][CH2:4][CH2:3][NH2:2])[CH:17]=[CH:9][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 962WaterHCID 79772-ChloropyridineHCID 9082Cysteamine HydrochlorideHCID 24758Sodium hydrideHCID 312751,4-Dioxane

Product 1

HCID 37013Phenyl-2-aminoethyl sulfide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 2-aminoethanethiol hydrochloride (4.07 g, 35.6 mmol) in dioxane (75 mL) at 50° C. Add sodium hydride (60% in mineral oil, 2.84 g, 71.0 mmol) at room temperature under nitrogen. Stir the reaction for 5 minutes. Add 2-chloropyridine (3.5 mL, 37 mmol) to the mixture. Reflux the mixture for 24 hours, and then cool to room temperature. Add water (100 mL), and methylene chloride (300 mL) to this mixture. Extract the aqueous layer with methylene chloride (3×50 mL). Wash the combined organic phase with brine (200 mL), dry (magnesium sulfate), filter and concentrate to an orange oil. Perform flash chromatography on silica gel eluting with 50% (80:18:12 CHCl3/MeOH/concentrated NH4OH)/methylene chloride to afford the title compound as a yellow oil (1.67 g) m/e=155 (MH+).

Workup

  1. customat room temperature
  2. customthe reaction for 5 minutes
  3. temperatureReflux the mixture for 24 hours
  4. extractionExtract the aqueous layer with methylene chloride (3×50 mL)
  5. washWash the combined organic phase with brine (200 mL)
  6. dry with materialdry (magnesium sulfate)
  7. filtrationfilter
  8. concentrationconcentrate to an orange oil

Sources & evidence

ORD record
ord-4745645f1acc45048e76e058ecfb6dac
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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