Water → N,N'-Dicyclohexylsulfamide

HRID 640030Notes

Reaction equation

HRID 640030 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[CH:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C([N:15]([CH2:18][CH3:19])CC)C.O>ClCCl>[CH:6]1([NH:12][S:1]([NH:15][CH:18]2[CH2:19][CH2:8][CH2:7][CH2:6][CH2:11]2)(=[O:3])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 24648Sulfuryl chloride

Product 1

HCID 12765315N,N'-DicyclohexylsulfamideYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a solution of 98.5% sulfuryl chloride (10.0 mL, 121 mmol) in 40 mL of dichloromethane is added dropwise at 0° C. to a solution of cyclohexylamine (30.0 g, 303 mmol) and triethylamine (84 mL, 606 mmol) in 150 mL of dichloromethane. The reaction mixture is stirred 4 hours at 0° C., neutralized with water, and diluted in dichloromethane (300 mL). The organic components are successively washed with diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue is suspended in ether, filtered through Büchner, and the precipitate is washed two times with 100 ml of ether to yield white crystals of N,N′-bis(cyclohexyl)sulfamide (14.0 g, 45%).

Workup

  1. washThe organic components are successively washed
  2. additionwith diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltered through Büchner
  6. washthe precipitate is washed two times with 100 ml of ether

Sources & evidence

ORD record
ord-fd3f66bf12a84fbca4bf1cbeb62df1eb
Source dataset
uspto-grants-2010_04
Patent number
US07691929B2

Reaction notes

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