Methanethiol → HCID 12044052, compound

HRID 1018066Notes

Reaction equation

HRID 1018066 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH2:18].[CH3:19][SH:20]>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([S:20][CH3:19])[CH:10]([OH:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 1118Sulfuric AcidHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 12044052HCID 12044052, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, 15.0 g of water, and 60.0 g of acetone in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at room temperature with irradiation by 500W Xe lamps (UXL-500D xenon lamp produced by Ushio). 14.4 g (0.3 mol) of methanethiol (produced by produced by Aldrich Chemical Co., Inc.) was continuously added to the reaction mixture and stirred for 5 hours under reflux. After completion, acetone and excess diethylamine were evaporated under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 14.3 g of 1-benzyl-4-methylthio-3-pyrrolidinol (yield 63.9%) was obtained.

Workup

  1. stirringstirred for 5 hours
  2. temperatureunder reflux
  3. customAfter completion, acetone and excess diethylamine were evaporated under reduced pressure
  4. extractionextracted with toluene and water
  5. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ba671b317a84cd5bb67c7dc1dee1543
Source dataset
uspto-grants-2002_11
Patent number
US06479668B1

Reaction notes

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