Hydrochloric Acid → N-(2,4-dimethoxybenzyl)-3,4-difluorobenzenesulfonamide

HRID 337732Notes

Reaction equation

HRID 337732 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].N1C=CC=CC=1.[F:19][C:20]1[CH:21]=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1[F:26].Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][S:27]([C:22]1[CH:23]=[CH:24][C:25]([F:26])=[C:20]([F:19])[CH:21]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 5972502,4-DimethoxybenzylamineHCID 27369133,4-Difluorobenzene-1-sulfonyl chloride

Product 1

HCID 89962551N-(2,4-dimethoxybenzyl)-3,4-difluorobenzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-dimethoxybenzylamine (3.35 mL, 22.3 mmol) and pyridine (9.02 mL, 111.5 mmol) in dichloromethane (75 mL), 3,4-difluorobenzenesulfonyl chloride (3.04 mL, 22.3 mmol) was added with cooling on ice, and the reaction solution was stirred at room temperature for 16 hours. To the reaction solution, 2 M hydrochloric acid (100 mL) was added, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate and vacuum concentrated to yield the title compound (7.66 g, 99%) as a colorless solid.

Workup

  1. temperaturewith cooling on ice
  2. extractionan organic layer was extracted
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate and vacuum
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-96b055b881cc4de09baae01a2ea3a2b1
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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