Sodium Chloride → HCID 14999092, compound

HRID 1030556Notes

Reaction equation

HRID 1030556 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][N:14]1[C:18](=[O:19])[CH2:17][S:16][CH:15]1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.Br[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[I-].[Na+].[Na+].[Cl-]>CCCCCC.O1CCCC1>[CH:28]1([CH2:27][C:17]2([CH2:11][CH:10]3[CH2:3][CH2:1][CH2:2][CH2:8][CH2:9]3)[S:16][CH:15]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[N:14]([CH3:13])[C:18]2=[O:19])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

9

Reactant 6

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 7912DiisopropylamineHCID 137636Cyclohexane, (bromomethyl)-HCID 14999087HCID 14999087, compoundHCID 178418339Butyllithium

Product 1

HCID 14999092HCID 14999092, compoundYield 4.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Dry diisopropylamine (2.76 ml, 15.8 mmol) was added to dry tetrahydrofuran (9 ml). Further a n-butyllithium solution (10.6 ml, 16.2 mmol) in hexane was added dropwise at -20° to -30° C. The mixture was kept between those temperatures for 1 hour. Then a solution of 3-methyl-2-(3-pyridyl)thiazolidin-4-one (3 g, 15.4 mmol) in dry tetrahydrofuran was added dropwise at -78° C. After this reaction mixture had been kept at the same temperature for 1 hour, bromomethylcyclohexane (3.01 g, 17.0 mmol) and sodium iodide (2.31 g, 15.4 mmol) were added at -78° C. This reaction mixture was heated up to room temperature and kept standing overnight. The resulting mixture, after addition of aqueous NaCl, was extracted with ethyl acetate. The extract was washed with aqueous NaCl, dried, and the solvent was removed in vitro. The residue was chromatographed on silica gel, giving 5,5-di(cyclohexylmethyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one (250 mg, 4.2% yield). IR (CHCl3) [cm-1 ]; 2920, 1675, 1640, 1390.

Workup

  1. waitAfter this reaction mixture had been kept at the same temperature for 1 hour
  2. waitkept standing overnight
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with aqueous NaCl
  5. customdried
  6. customthe solvent was removed in vitro
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-fe7eb9c918484a92a36479314d7de940
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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