Thiophenol → HCID 70577630, compound

HRID 1413826Notes

Reaction equation

HRID 1413826 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[C:2]1([CH2:1][N:8]2[CH2:9][C@@H:10]([S:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:11]([OH:13])[CH2:12]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 70577630HCID 70577630, compound

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A mixture of 8.8 g. (0.05 mole) of 1-benzyl-3,4-epoxypyrrolidine, 6.0 g. (0.055 mole) of thiophenol, and 3 drops of water was heated on a steam bath overnight. Upon cooling the mixture, a solid crystallized. The solid was dissolved in methylene chloride and the methylene chloride solution was washed with two 50-ml portions of 5% sodium hydroxide. The methylene chloride layer was dried over anhydrous sodium sulfate and concentrated to give a yellow oil which solidified on standing. The solid was recrystallized from cyclohexane to give 8.6 g. (60%) of a tan solid, m.p. 97°-99°.

Workup

  1. additionA mixture of 8.8 g
  2. temperatureUpon cooling the mixture
  3. customa solid crystallized
  4. dissolutionThe solid was dissolved in methylene chloride
  5. washthe methylene chloride solution was washed with two 50-ml portions of 5% sodium hydroxide
  6. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give a yellow oil which
  9. customThe solid was recrystallized from cyclohexane
  10. customto give 8.6 g

Sources & evidence

ORD record
ord-8b3209f6e18046819d951319c4dd9b9e
Source dataset
uspto-grants-1981_02
Patent number
US04251541

Reaction notes

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