Ethanesulfonyl chloride → N-(4-nitrobenzyl)ethanesulfonamide

HRID 1428765Notes

Reaction equation

HRID 1428765 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12]([S:14](Cl)(=[O:16])=[O:15])[CH3:13]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][NH:11][S:14]([CH2:12][CH3:13])(=[O:16])=[O:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 291474-Nitrobenzylamine

Product 1

HCID 47372696N-(4-nitrobenzyl)ethanesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(4-Nitrophenyl)methanamine (715 mg, 4.7 mmol) was dissolved in pyridine (4 mL). The reaction mixture was added ethane sulfonyl chloride (0.58 mL, 6.11 mmol) and stirred for 1 h at room temperature. TLC showed complete consumption of starting material. The mixture was diluted with 1N HCl and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give N-(4-nitrobenzyl)ethanesulfonamide (776 mg, 68%).

Workup

  1. customconsumption of starting material
  2. additionThe mixture was diluted with 1N HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-b6324124c0b84b039676ca1eb4678409
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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