Aniline → Benzenesulfonamide, 4-methyl-N-phenyl-

HRID 1587544

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

Dissolve aniline (930 mg, 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

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

Sources & evidence

ORD record: ord-17afee4eb84643fa9f4983b8a056dfdb
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05217964

Linked notes

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