Sodium Hydroxide → 1-Chloro-3-(4-aminothiophenoxy)propane

HRID 1030279Notes

Reaction equation

HRID 1030279 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[OH-].[Na+]>CCO>[Cl:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 149330551-[(3-Chloropropyl)sulfanyl]-4-nitrobenzene

Product 1

HCID 149330561-Chloro-3-(4-aminothiophenoxy)propaneYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-3-(4-nitrothiophenoxy)propane (1.00 g, 4.32 mmmol), stannous chloride dihydrate (4.87 g, 21.58 mmol), and EtOH was heated under reflux for 3 hours. The mixture was cooled, 2.5 N NaOH (21 mL) was added, and the precipitate was removed by filtration. The filtrate concentrated to 10 mL and extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 855 mg (98%) of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate concentrated to 10 mL
  6. extractionextracted with EtOAc
  7. dry with materialThe extracts were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8696b63610f340619c3059108fbd978d
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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