4-Toluenesulfonyl chloride → 4-Methylbenzenesulfonic acid 4-(4-acetylaminophenyl)butyl ester

HRID 65224Notes

Reaction equation

HRID 65224 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>N1C=CC=CC=1>[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 185045324-(Acetylamino)benzenebutanol

Product 1

HCID 538442024-Methylbenzenesulfonic acid 4-(4-acetylaminophenyl)butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 0° C. solution of 4.5 g (0.022 mole) 4-(acetylamino)benzenebutanol in 25 ml pyridine, add 8.3 g (0.044 mole) tosyl chloride and chill in the refrigerator overnight. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 90:10). At the completion of the reaction, pour the reaction mixture onto 500 ml ice water and stir for 15 minutes. Extract the aqueous mixture with 3×300 ml ether. Wash the combined organic layers with 1N hydrochloric acid, then with water, dry over potassium carbonate, filter and remove the solvent in vacuo to obtain the title compound.

Workup

  1. temperaturechill in the refrigerator overnight
  2. customthe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 90:10)
  3. customAt the completion of the reaction
  4. extractionExtract the aqueous mixture with 3×300 ml ether
  5. washWash the combined organic layers with 1N hydrochloric acid
  6. dry with materialwith water, dry over potassium carbonate
  7. filtrationfilter
  8. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-6072f8e986394fa2bd99331cd89b6304
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

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