1-Hexadecanesulfonyl chloride → N-[7-(dimethylamino)heptyl]-1-hexadecanesulfonamide

HRID 621769

Reaction equation

HRID 621769 reaction equation
[CH2:1]([S:17](Cl)(=[O:19])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:21][N:22]([CH3:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH2:30]>O1CCCC1>[CH3:31][N:22]([CH3:21])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][S:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 969231-Hexadecanesulfonyl chlorideHCID 3822076(7-Aminoheptyl)dimethylamine

Product 1

HCID 14407599N-[7-(dimethylamino)heptyl]-1-hexadecanesulfonamideYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

650 mg (2 meq) of hexadecanesulfonylchloride are added dropwise to 744 mg (4 meq) of 7-dimethylaminoheptylamine stirring in tetrahydrofuran at 0° C. The reaction mixture is evaporated under reduced pressure (<30° C.) dried in vacuo, and chromatographed on silica gel in the system CH2Cl2 :CH3OH:NH4OH (65:25:4) and fractions 47-52 having Rf 0.9 on TLC S.G. CH2Cl2 :CH3OH:NH4OH are combined, evaporated under reduced pressure <30° C. and dried in vacuo to yield 300 mg of title compound having a m.p. of 56°-57.5° C. uncorr.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure (<30° C.)
  2. customdried in vacuo
  3. customchromatographed on silica gel in the system CH2Cl2 :CH3OH:NH4OH (65:25:4) and fractions 47-52 having Rf 0.9 on TLC S.G
  4. customevaporated under reduced pressure <30° C.
  5. customdried in vacuo

Sources & evidence

ORD record
ord-01ab017c257f415c9679c2afc28f6aec
Source dataset
uspto-grants-1989_04
Patent number
US04824996

Linked notes

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