Thiirane → HCID 21411767, compound

HRID 2071654Notes

Reaction equation

HRID 2071654 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[CH2:12]1[S:14][CH2:13]1.[Cl-].[NH4+]>N>[N:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:9][CH2:10][OH:11])[CH2:12][CH2:13][SH:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 9865ThiiraneHCID 25517Ammonium ChlorideHCID 729234-PyridinepropanolHCID 5360545Sodium

Product 1

HCID 21411767HCID 21411767, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by sodium metal (6.3 gms) in small pieces. The mixture was allowed to stand for 30 minutes and 3-(4-pyridyl)-propan-1ol (19 gms) was then added. A deep yellow colour was allowed to develop over a period of 2 hours after which time ethylene sulphide (8.3 gms) was added quickly. A vigorous reaction occurred and the mixture was stirred for a further 4 hours. Ammonium chloride (10 gms) was added and the solvent was allowed to evaporate overnight. The residual tacky solid was extracted into pyridine and the mixture was filtered and the solvent evaporated. Distillation of the residual oil yielded 3-(4-pyridyl)-5-hydroxy-pentane-1-thiol (12.7 gms, 60% conversion); b.p. 177°-185° C/1 mm Hg, m.p. 50°-52° C, characterised by the following spectra:

Workup

  1. waitto develop over a period of 2 hours
  2. customA vigorous reaction
  3. customto evaporate overnight
  4. extractionThe residual tacky solid was extracted into pyridine
  5. filtrationthe mixture was filtered
  6. customthe solvent evaporated
  7. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-e87bd1ca2066450f927913a7917c2d86
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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