Triethylamine → N-cyclohexyl-N'-hexadecylsulfamide

HRID 640032

Reaction equation

[CH:1]1([NH:7][S:8](Cl)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:12]([NH2:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH:1]1([NH:7][S:8]([NH:28][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 13.6 g of the cyclohexylsulfamoyl chloride (69 mmol) in 100 mL of dichloromethane is added under argon atmosphere to a solution of 1-hexadecylamine (19.9 g, 82 mmol) and triethylamine (47.5 mL, 340 mmol) in 300 mL of dichloromethane. The reaction mixture is stirred 5 hours at 0° C., neutralized with an aqueous Na2CO3 solution and concentrated under reduced pressure. The residue is taken up in dichloromethane (800 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 a white powder of N-cyclohexyl-N′-hexadecylsulfamide (21.8 g, 79%).

Workup

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

Sources & evidence

ORD record: ord-2ce0015573b343abbf3d7d36d0f5e3e1
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691929B2

Linked notes

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