Carbon Tetrachloride → HCID 14999113, compound

HRID 1493240Notes

Reaction equation

HRID 1493240 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH2:22][N:23]1[C:27](=[O:28])[CH:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[S:25][CH:24]1[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1.C(Cl)(Cl)(Cl)[Cl:45]>>[Cl:45][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[CH:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[S:25][CH:24]1[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 14999112HCID 14999112, compound

Product 1

HCID 14999113HCID 14999113, compoundYield 80%

Procedure

Triphenylphosphine (3.44 g, 13 mmol) was added to a mixture of 3-(2-hydroxyethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one (3.49 g, 10 mmol) and carbon tetrachloride (20 ml) with stirring at room temperature. Then the mixture was refluxed with stirring for 2.5 hours. The product mixture was cooled and filtered to remove the formed crystals. The filtrate was concentrated and chromatographed, giving the cis-isomer (0.55 g) and trans-isomer (1.46 g) of the title compound and a mixture of two isomers (0.94 g) (total 2.95 g, 80% yield).

Workup

  1. temperatureThen the mixture was refluxed
  2. stirringwith stirring for 2.5 hours
  3. temperatureThe product mixture was cooled
  4. filtrationfiltered
  5. customto remove the formed crystals
  6. concentrationThe filtrate was concentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-70bba3a3c6a6418886b589dd56d47aa5
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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