Sodium hydride → N-Ethyl-N-(3-chloropropyl)-p-toluenesulfonamide

HRID 361697Notes

Reaction equation

HRID 361697 reaction equation
C1(C)C=CC(S([C:10](S(C2C=CC(C)=CC=2)(=O)=O)([CH2:32][CH2:33]NCCCCNCCCN)[N:11]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])S(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.[H-].[Na+].[CH3:57][CH2:58]O.C(Cl)(Cl)[Cl:61]>CN(C=O)C.[I-].[K+]>[CH2:57]([N:11]([CH2:10][CH2:32][CH2:33][Cl:61])[S:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1)(=[O:23])=[O:24])[CH3:58]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 21889567Chloroform ethanolHCID 23440082Tetratosylspermine

Product 1

HCID 14056762N-Ethyl-N-(3-chloropropyl)-p-toluenesulfonamideYield 60%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

3, 7, 11, 16, 20, 24-Hexa(p-toluenesulfonyl)3, 7, 11, 16, 20, 24-hexaazahexacosane. To tetra (p-toluenesulfonyl) spermine (1.02 g, 2.22 mmol) in dry DMF (10 mL) is added sodium hydride (80% in oil, 0.21 g, 7.0 mmol) and potassium iodide (53 mg, 0.32 mmol). After 30 minutes, N-ethyl-t4-(3-chloropropyl)-p-toluenesulfonamide (2.9 g, 10.5 mmol) in DMF (10 mL) is introduced and the mixture is stirred for 20 h at room temperature then heated at 40°-50° C. for 2 h. The cooled reaction mixture is poured Into ice-cold 5% NaOH (100 mL), which is extracted with CHCl3 (3×). A water wash, then solvent removal (rotovap then Kugelrohr distillation) yields crude hexatosylamide. Silica gel chromatography (1% EtOH/CHCl3) affords 1.73 g of product (60%). NMR δ1.08 (t, 6H), 1.45-2.10 (m, 12H), 2.34 (s, 10H), 2.96-3.37 (m, 24H), 7.2-7.8 (m, 24H).

Workup

  1. temperaturethen heated at 40°-50° C. for 2 h
  2. customThe cooled reaction mixture
  3. extractionis extracted with CHCl3 (3×)
  4. washA water wash
  5. customsolvent removal (rotovap
  6. distillationKugelrohr distillation)
  7. customyields crude hexatosylamide

Sources & evidence

ORD record
ord-fe4910e2d1c84397b0c00eeccbf09a28
Source dataset
uspto-grants-1999_02
Patent number
US05866613

Reaction notes

Loading…