Thiirane → HCID 21411761, compound

HRID 2071653Notes

Reaction equation

HRID 2071653 reaction equation
[Na].[CH2:2]([O:4][CH:5]([O:14][CH2:15][CH3:16])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH3:3].[CH2:17]1[S:19][CH2:18]1.[Cl-].[NH4+]>N>[N:11]1[CH:12]=[CH:13][C:8]([CH:7]([CH2:6][CH:5]([O:4][CH2:2][CH3:3])[O:14][CH2:15][CH3:16])[CH2:17][CH2:18][SH:19])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 9865ThiiraneHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 21411769HCID 21411769, compound

Product 1

HCID 21411761HCID 21411761, compoundYield 66%

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)-propionaldehyde diethyl acetal (20.0 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 filtered and the solvent was evaporated from the filtrate. Distillation of the residual oil yielded 3-(4-pyridyl)-5,5-diethoxy-pentane-1-thiol (17 gms, 63% conversion) b.p. 167°-172° C/1 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. filtrationfiltered
  6. customthe solvent was evaporated from the filtrate
  7. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-ada825d0e1f34a24ab1e79cb475fed83
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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