4-Toluenesulfonyl chloride → Benzenesulfonamide, 4-methyl-N-octyl-

HRID 1955121Notes

Reaction equation

HRID 1955121 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([NH2:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>ClCCl.O>[CH2:12]([NH:20][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 8143Octylamine

Product 1

HCID 3090479Benzenesulfonamide, 4-methyl-N-octyl-Yield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of toluene-4-sulfonyl chloride (5.0 g, 0.026 mol) in dry dichloromethane (150 ml) was cooled to 0° C. during the dropwise addition of n-octylamine (9.6 ml, 0.058 mol) with stirring over 4 minutes. The reaction mixture was then allowed to stir for 30 minutes before being diluted with dichloromethane (200 ml) and water (200 ml). The organic layer was separated and washed consecutively with 1M HCl, 0.5M Na2CO3 and brine before being dried over anhydrous Na2SO4. The solution was filtered and concentrated in vacuo to a crude solid which was purified by flash chromatography (silica gel, 11% ethyl acetate in hexane) to give the title compound as a white solid (7.0 g, 94%). This material was then used immediately in the next step.

Workup

  1. stirringto stir for 30 minutes
  2. customThe organic layer was separated
  3. washwashed consecutively with 1M HCl, 0.5M Na2CO3 and brine
  4. dry with materialbefore being dried over anhydrous Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo to a crude solid which
  7. customwas purified by flash chromatography (silica gel, 11% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6dc4214ebde6426499ae76a832aa6267
Source dataset
uspto-grants-2000_09
Patent number
US06124332

Reaction notes

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