Potassium Hydroxide → 178243-37-3

HRID 1925632Notes

Reaction equation

HRID 1925632 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[CH3:8][C:9]1([CH3:16])[CH2:14][CH2:13][C:12](=[CH2:15])[CH2:11][CH2:10]1.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[K+]>C(OCC)C>[CH3:8][C:9]1([CH3:16])[CH2:14][CH2:13][C:12]2([NH:5][C:6](=[O:7])[CH2:15]2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 61475Sodium Thiosulfate PentahydrateHCID 70918Chlorosulfonyl isocyanate3×HCID 5729646007-96-1

Product 1

HCID 59718832178243-37-3Yield 60.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chlorosulfonyl isocyanic acid (0.67 mL, 7.7 mmol) was dropped into the dehydrated diethyl ether (11 mL) solution of 1,1-dimethyl-4-methylene-cyclohexane (0.91 g, 7.4 mmol), which had been obtained in 1), in an ice bath. The reaction mixture was stirred at room temperature for 1 hour, and chlorosulfonyl isocyanic acid (0.67 mL, 7.7 mmol) was added in the reaction required in the ice bath and further stirred at room temperature for 1 hour. After chlorosulfonyl isocyanic acid (0.32 mL, 3.7 mmol) had been added in the reaction mixture in the ice bath and further stirred at room temperature for 2 hours, the aqueous solution (4.5 mL) containing sodium thiosulfate pentahydrate (4.56 g, 18.4 mmol) and 10% potassium hydroxide solution was added alternately in the reaction mixture in the ice bath and the pH was adjusted to be about 10, and then the reaction mixture was stirred for 2 hours. The insoluble matter was removed by filtration, and the filtrate was extracted with chloroform. Then the organic layer was washed with water and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and a colorless solid (0.75 g) was obtained.

Workup

  1. customhad been obtained in 1), in an ice bath
  2. stirringfurther stirred at room temperature for 1 hour
  3. stirringfurther stirred at room temperature for 2 hours
  4. stirringthe reaction mixture was stirred for 2 hours
  5. customThe insoluble matter was removed by filtration
  6. extractionthe filtrate was extracted with chloroform
  7. washThen the organic layer was washed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-83db3dfbbbe841079927cf0fb04eedb6
Source dataset
uspto-grants-2012_05
Patent number
US08178681B2

Reaction notes

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