o-Chlorothiophenol → HCID 70578220, compound

HRID 1413827Notes

Reaction equation

HRID 1413827 reaction equation
[CH2:1]([N:3]1[CH2:7][CH:6]2[O:8][CH:5]2[CH2:4]1)[CH3:2].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16]>Cl.C(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][C@@H:5]1[CH2:4][N:3]([CH2:1][CH3:2])[CH2:7][C@H:6]1[OH:8]

Participants

5

Reactant 2

HCID 80599o-ChlorothiophenolHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 70578220HCID 70578220, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.3 g. (0.1 mole) of crude 1-ethyl-3,4-epoxypyrrolidine, 14.4 g. (0.1 mole) of 2-chlorothiophenol and 1 drop concentrated hydrochloric acid on a steam bath overnight. The reaction mixture was dissolved in methylene chloride and the solution was washed with two 100-ml portions of 5% sodium hydroxide and once with water. The methylene chloride layer was dried over anhydrous sodium sulfate and concentrated to give 23.8 g. of dark oil as residue which solidified when scratched with petroleum ether. The solid was collected by filtration and recrystallized from cyclohexane to yield 10 g. (39%) of tan solid, m.p. 90.5°-92.5°.

Workup

  1. additionA mixture of 11.3 g
  2. customovernight
  3. washthe solution was washed with two 100-ml portions of 5% sodium hydroxide and once with water
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give 23.8 g
  7. filtrationThe solid was collected by filtration
  8. customrecrystallized from cyclohexane
  9. customto yield 10 g

Sources & evidence

ORD record
ord-7fd92bd79cd9470da9589b2f1d2b1d69
Source dataset
uspto-grants-1981_02
Patent number
US04251541

Reaction notes

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