Triethylamine → N-(4-nitrobenzyl)ethanesulfonamide

HRID 2236927Notes

Reaction equation

HRID 2236927 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH2:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20]>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:21]([CH2:19][CH3:20])(=[O:23])=[O:22])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 291474-Nitrobenzylamine

Product 1

HCID 47372696N-(4-nitrobenzyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitro-benzylamine (47.2 mg, 0.25 mmol) in THF (250 μL) is added triethylamine (89 μL) and ethyl sulfonyl chloride (24 μL, 0.25 mmol). The reaction mixture is shaken at ambient temperature for 16 hours. The reaction mixture is then concentrated, methanol is added followed by Novabiochem AM resin to remove unreacted amine. This is then shaken for two hours, filtered, concentrated to yield ethanesulfonic acid 4-nitro-benzylamide, which is used as such for the subsequent reaction.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. additionmethanol is added
  3. customto remove unreacted amine
  4. stirringThis is then shaken for two hours
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d2d555e3477249118584d7f3fb0c8a7f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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