Benzenesulfonyl chloride → N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide

HRID 660645Notes

Reaction equation

HRID 660645 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH2:12]CN)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([N:23](CC)CC)C.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH2:12][N:23]([CH3:21])[S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:36])=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 18184526(3-Benzyloxy-4-nitrobenzyl)methylamine

Product 1

HCID 68840966N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-benzyloxy-4-nitrobenzyl)methylamine (1.00 g, 3.672 mmol) and triethylamine (0.56 mL, 4.04 mmol) in CH2Cl2 (20 mL) is added dropwise benzenesulfonyl chloride (0.515 mL, 4.04 mmol) and the reaction is heated at reflux for 1 h. After cooling to RT, the reaction is diluted with CH2Cl2 (75 mL). The solution is washed with 1N HCl, saturated sodium bicarbonate, dried over Na2SO4, filtered, and concentrated under vacuum to afford an orange oil. The oil is triturated with ether to afford the title compound: (M+1)+=413.

Workup

  1. temperaturethe reaction is heated
  2. temperatureat reflux for 1 h
  3. washThe solution is washed with 1N HCl, saturated sodium bicarbonate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto afford an orange oil
  8. customThe oil is triturated with ether

Sources & evidence

ORD record
ord-27376899a7bd49fcbe3fe28e050c1226
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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