4-Toluenesulfonyl chloride → HCID 3425930, compound

HRID 1587551Notes

Reaction equation

HRID 1587551 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 660384-(Methylthio)aniline

Product 1

HCID 3425930HCID 3425930, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

Dissolve 4-(methylmercapto) aniline (1.39 g, 10 mmol) in anhydrous pyridine (25 mL) and cool to 5° C. Add, by dropwise addition, p-toluenesulfonyl chloride (2.1 g, 11 mmol) and stir overnight. Partition between water and ethyl acetate and separate the organic phase. Wash the organic phase with cold 1N hydrochloric acid, saturated sodium hydrogen carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound.

Workup

  1. customPartition between water and ethyl acetate
  2. customseparate the organic phase
  3. washWash the organic phase with cold 1N hydrochloric acid, saturated sodium hydrogen carbonate and brine
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-f9f046582442439a8a0c6a42e0f9537f
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

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