4-Toluenesulfonyl chloride → HCID 10846183, compound

HRID 1600429Notes

Reaction equation

HRID 1600429 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH2:16])=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:16]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 983750412-Methoxydodecanamide

Product 1

HCID 10846183HCID 10846183, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the title compound of Example 12 (5.0 g, 22 mmol) in 30 mL pyridine at 0° C. was added in portions p-toluenesulfonyl chloride (5.1 g, 27 mmol). After stirring at room temperature for 3 days, the reaction mixturewas filtered, the cake washed with methylene chloride and the filtrate concentrated. The resulting residue was dissolved in methylene chloride, washed successively with 1N HCl, water, saturated NaHCO3, water and brine, dried with magnesium sulfate, filtered and concentrated. Chromatography of the crude product on silica gel using 20-80 diethyl ether-hexane as eluant gave the title compound (3.4 g) as a pale yellow liquid. The structure was supported by NMR, infrared spectroscopy, elemental analysis and mass spectroscopy.

Workup

  1. washthe reaction mixturewas filtered, the cake washed with methylene chloride
  2. concentrationthe filtrate concentrated
  3. dissolutionThe resulting residue was dissolved in methylene chloride
  4. washwashed successively with 1N HCl, water, saturated NaHCO3, water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2446c8b3c3564cc39283767849109a32
Source dataset
uspto-grants-1998_04
Patent number
US05744631

Reaction notes

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