Thiirane → HCID 21411776, compound

HRID 2071655Notes

Reaction equation

HRID 2071655 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:4][CH:3]=1.[CH2:16]1[S:18][CH2:17]1.[Cl-].[NH4+]>N>[N:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH2:16][CH2:17][SH:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 9865ThiiraneHCID 25517Ammonium ChlorideHCID 459510HCID 459510, compoundHCID 5360545Sodium

Product 1

HCID 21411776HCID 21411776, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by sodium metal (2.3 gms) in small pieces. The mixture was allowed to stand for 30 minutes and 3-(4-pyridyl)-1-diethylamino propane (19.2 gms) was then added. A deep yellow colour was allowed to develop over a period of 2 hours, after which time ethylene sulphide (6.0 gms) was added quickly. A vigorous reaction occurred and the mixture was stirred for a further 5 hours. Ammonium chloride (7 gms) was added, and the solvent was allowed to evaporate overnight. The residual tacky solid was extracted into pyridine and the extract was filtered and the solvent evaporated. Distillation of the residual oil-yielded 3-(4-pyridyl)-5-diethylamino-pentane-1-thiol, (18 gms, 72% conversion) b.p. 140°-143° C/0.2 mm Hg, 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 extract was filtered
  6. customthe solvent evaporated
  7. distillationDistillation of the

Sources & evidence

ORD record
ord-a48b95ea81da4288baeb14225e7125d0
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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