Sodium Chloride → HCID 14999092, compound

HRID 981556Notes

Reaction equation

HRID 981556 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 vacuo. 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).

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 vacuo
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-54cc5bfb5c544ae1910ed5e6dbd34875
Source dataset
uspto-grants-1991_02
Patent number
US04992455

Reaction notes

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