Hydrochloric Acid → HCID 178444343, compound

HRID 429709Notes

Reaction equation

HRID 429709 reaction equation
[Mg].[CH2:2]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][CH3:6].[C:20](=[S:22])=[S:21].Cl>C1COCC1>[CH2:2]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([C:20]([SH:22])=[S:21])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 5462224MagnesiumHCID 178444243HCID 178444243, compound

Product 1

HCID 178444343HCID 178444343, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension prepared by suspending 0.95 g (39 mmol) of magnesium in 200 ml of THF was added dropwise a solution prepared by dissolving 9.28 g (30 mmol) of 4-(trans-4-n-pentylcyclohexyl) bromobenzene in 80 ml of THF, at room temperature while being stirred in 1 hour, and then heated to reflux for 2 hours to prepare a Grignard reagent. To this solution was added dropwise 5.7 g (75 mmol) of carbon disulfide at room temperature in 30 min and stirred as it was overnight. To this reaction solution was added 150 ml of 1M hydrochloric acid to terminate the reaction and extracted with 350 ml of toluene. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under a reduced pressure, and the residue was recrystallized from heptane to obtain 4.74 g of 4-(trans-4-n-pentylcyclohexyl)phenyldithiocarboxylic acid (yield 51.5%).

Workup

  1. customTo a suspension prepared
  2. additionwas added dropwise a solution
  3. customprepared
  4. temperatureheated
  5. temperatureto reflux for 2 hours
  6. stirringstirred as it
  7. waitwas overnight
  8. customto terminate
  9. customthe reaction
  10. extractionextracted with 350 ml of toluene
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under a reduced pressure
  13. customthe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-da0fcebf428b424c8c380210cb5aaf11
Source dataset
uspto-grants-2001_11
Patent number
US06319570B1

Reaction notes

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