Acetic Acid → N,N-diethyl-N-heptyl-4-[(methylsulfonyl)amino]benzeneethanaminium bromide

HRID 466364

Reaktionsgleichung

Reaktionsgleichung von HRID 466364
[CH2:1]([N:3]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1)[CH3:2].[CH3:24][C:25]1C=C(C(=O)C)C=CC=1NS(C)(=O)=O.CC(O)=O.C([Br:45])C>C(#N)C>[Br-:45].[CH2:1]([N+:3]([CH2:24][CH3:25])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])=[CH:8][CH:7]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6332Ethyl Bromide2×HCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamideHCID 53740092N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide

Produkt 1

HCID 19873396N,N-diethyl-N-heptyl-4-[(methylsulfonyl)amino]benzeneethanaminium bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A stirred solution of N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide as prepared in Example 3 (0.332 g, 0.975 mmol) in acetonitrile (3 ml) is treated with HOAc, (0.056 ml, 0.975 mmol) and ethyl bromide (0.73 ml, 9.75 mmol). The solution is refluxed for 1 day, treated with additional ethyl bromide (1 ml) and acetonitrile (3 ml) and refluxed for one additional day. The mixture is concentrated; the residue is mixed with a solution of NaHCO3 (160 mg) in water and extracted with Et2O. The extracts are washed with water, dried (MgSO4) and concentrated to give recovered starting material (0.15 g, identified by TLC). The aqueous layers are combined, made strongly basic with 1N KOH, saturated with potassium bromide and washed with CH2Cl2. The aqueous layer is then acidified with 48% hydrogen bromide and extracted with CH2Cl2. The extracts are washed with saturated potassium bromide, dried (NaSO4) and concentrated to give 0.15 g of N,N-diethyl-N-heptyl-4-[(methylsulfonyl)amino]benzeneethanaminium bromide. MS calc'd for C20H37N2O2S (M+): 369.2576. Found: 369.2585.

Aufarbeitung

  1. temperatureThe solution is refluxed for 1 day
  2. temperaturerefluxed for one additional day
  3. concentrationThe mixture is concentrated
  4. additionthe residue is mixed with a solution of NaHCO3 (160 mg) in water
  5. extractionextracted with Et2O
  6. washThe extracts are washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give
  10. customrecovered
  11. washwashed with CH2Cl2
  12. extractionextracted with CH2Cl2
  13. washThe extracts are washed with saturated potassium bromide
  14. dry with materialdried (NaSO4)
  15. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e6e6ab513b7f4085a6d7b165e9cd6194
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155268

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