4-Toluenesulfonyl chloride → HCID 19980957, compound

HRID 1494445Notes

Reaction equation

HRID 1494445 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[CH2:1]([N:5]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])[S:36]([C:33]1[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=1)(=[O:38])=[O:37])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 18407387N-Butyl-2,4-difluorobenzenamine

Product 1

HCID 19980957HCID 19980957, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of 14.8 g of N-butyl-2,4-difluoroaniline, 16.2 g of triethylamine and 0 5 g of dimethylaminopyridine in 150 ml of toluene is treated dropwise at 0-5° C. with a solution of 15.2 g of p-toluenesulphonyl chloride in 80 ml of toluene. The reaction mixture is then warmed to 90° C. and stirred at this temperature for 48 hours. After cooling, the mixture is washed with 5% strength HCl and with water, and the toluene solution is dried over Na2SO4 and evaporated. The residue is distilled at 0.01 mbar. 18.5 g of N-butyl-N-(2,4-difluorophenyl)-p-toluenesulphonamide are obtained at 150°-160° as a colourless oil.

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed with 5% strength HCl and with water
  3. dry with materialthe toluene solution is dried over Na2SO4
  4. customevaporated
  5. distillationThe residue is distilled at 0.01 mbar

Sources & evidence

ORD record
ord-6086daad30234144b178280afea8f671
Source dataset
uspto-grants-1991_06
Patent number
US05026625

Reaction notes

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