Sodium Hydroxide → 1-[3-(Methylsulfanyl)propyl]-1H-pyrrole

HRID 1576274Notes

Reaction equation

HRID 1576274 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH2:6].CO[CH:9]1[CH2:13][CH2:12][CH:11](OC)O1.[OH-].[Na+]>C(O)(=O)C>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:9]=[CH:13][CH:12]=[CH:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 777433-(Methylthio)propylamineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 215117321-[3-(Methylsulfanyl)propyl]-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 25 g (0.36 mole) 3-(methylthio)-propylamine and 43 g (0.36 mole) 2,5-dimethoxytetrahydrofuran is placed in a 1-liter 3-neck flask equipped with a stirrer, addition funnel, thermometer and condenser, and 200 ml glacial acetic acid is added dropwise with stirring while maintaining the temperature below 20°C. The reaction mixture is refluxed for 30 minutes and, after cooling, it is made basic (pH 9-10) by the addition of 375 ml 30% aqueous sodium hydroxide and steam-distilled for 3 hours.

Workup

  1. customis placed in a 1-liter 3-neck flask
  2. customequipped with a stirrer, addition funnel
  3. temperaturewhile maintaining the temperature below 20°C
  4. temperatureThe reaction mixture is refluxed for 30 minutes
  5. temperatureafter cooling
  6. distillationsteam-distilled for 3 hours

Sources & evidence

ORD record
ord-f359eec4cf5547eeb25796d57625e05e
Source dataset
uspto-grants-1976_09
Patent number
US03980089

Reaction notes

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