Sodium hydride → HCID 19966068, compound

HRID 1734892Notes

Reaction equation

HRID 1734892 reaction equation
[H-].[Na+].[C:3]1([CH3:15])[CH:8]=[CH:7][C:6]([S:9]([CH2:12][S:13][CH3:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:16]1([CH2:22]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl-].[NH4+]>CCCCCC.CN(C)C=O>[CH3:15][C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH:12]([S:13][CH3:14])[CH2:22][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 137636Cyclohexane, (bromomethyl)-HCID 548421Methylthiomethyl p-tolyl sulfone

Product 1

HCID 19966068HCID 19966068, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

990 mg (22.7 mmol) of sodium hydride (as a 55% w/w suspension in mineral oil) were washed twice with hexane, and suspended in 40 ml of dimethylformamide. 4.35 g (20.1 mmol) of methylthiomethyl p-tolyl sulfone were added to this suspension and, after 5 minutes, 3.1 ml (22.2 mmol) of cyclohexylmethyl bromide were added. The mixture was allowed to return to room temperature, after which it was stirred for 5 hours. At the end of this time, a dilute aqueous solution of ammonium chloride was added to stop the reaction. The reaction mixture was then extracted with diethyl ether, and the extract was washed with a saturated aqueous solution of sodium chloride. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 100 g of silica gel. Elution with a 1:3 by volume mixture of ethyl acetate and hexane afforded 5.57 g (yield 89%) of the title compound as crystals, melting at 65°-66° C. (after recrystallization from a mixture of diisopropyl ether and hexane)

Workup

  1. customto return to room temperature
  2. customthe reaction
  3. extractionThe reaction mixture was then extracted with diethyl ether
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride
  5. customThe solvent was then removed by distillation under reduced pressure
  6. washElution with a 1:3
  7. additionby volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-31e45ace5e8c4234ae2b9ff2f2764ba8
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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