Sulfuric Acid → HCID 86743820, compound

HRID 1165718Notes

Reaction equation

HRID 1165718 reaction equation
[CH:1]([C:4]1([CH3:17])[C:8](=[S:9])[NH:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:5]1)([CH3:3])[CH3:2].C([Li])(CC)C.[Cl:23]C(Cl)(Cl)C(Cl)(Cl)Cl.[Cl-].[Na+].S(=O)(=O)(O)O>O1CCCC1.C1CCCCC1>[Cl:23][C:12]1[CH:11]=[C:10]([C:6]2[NH:7][C:8](=[S:9])[C:4]([CH:1]([CH3:3])[CH3:2])([CH3:17])[N:5]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 6214HexachloroethaneHCID 15017266HCID 15017266, compoundHCID 178418400CID 53628100

Product 1

HCID 86743820HCID 86743820, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

A mechanically stirred solution of 20.0 g of 4-isopropyl-4-methyl-2-p-tolyl-2-imidazolin-5-thione in 200 mL of dry tetrahydrofuran is treated dropwise with 160 mL of a 1.2M solution of sec-butyl lithium (0.191 mol) in cyclohexane over a 40 minute period at -72° to -65° C. After stirring the resulting solution at -40° to -35° for one and one-half hours, a solution of 21.4 g (0.090 mol) of hexachloroethane in 125 mL of dry tetrahydrofuran is added dropwise. Addition temperature is allowed to reach -20° C. After warming to room temperature over a 16 hour period, the reaction is treated with 200 mL of ice water plus 200 mL of a saturated sodium chloride solution. The mixture is carefully acidified to pH 3 with concentrated sulfuric acid. The phases are separated and the aqueous phase is extracted with 200 mL ether. The organic phases are combined, dried over magnesium sulfate and concentrated to an oily residue. The residue is purified by chromatography on silica gel to give pure 2-(2-chloro-p-tolyl)-4-isopropyl-4-methyl-2-imidazolin-5-thione.

Workup

  1. additionAddition temperature
  2. customto reach -20° C
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with 200 mL ether
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to an oily residue
  7. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c2d072ea22264e738f2de990ec2e28da
Source dataset
uspto-grants-1990_03
Patent number
US04911747

Reaction notes

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